


Alola, Mama!

by Scrib_eyeSteak



Series: Alola, Mama! : The Complete Nidoqueen Package [1]
Category: Pocket Monsters | Pokemon - All Media Types
Genre: 69 (Sex Position), Anal Sex, Author has a rain fetish, Bathroom Sex, Beach Sex, Chair Sex, Couch Sex, Dinner, Door Sex, F/M, Golf, Gym Sex, Hotel Sex, Kitchen Sex, MILFs, Outdoor Sex, Pool Sex, Public Blow Jobs, Sauna, Semi-Public Sex, Sexual Roleplay, Shower Sex, Wall Sex, jacuzzi
Language: English
Status: Completed
Published: 2019-06-08
Updated: 2019-07-27
Packaged: 2020-04-19 18:23:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 12
Words: 25,034
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19138198
Author URL: https://archiveofourown.org/users/Scrib_eyeSteak/pseuds/Scrib_eyeSteak
Summary: a very lucky ex-Skull winds up with the opportunity of a lifetime when he accepts an invitation to work at the Hano Grand on a very special project. Updates throughout June.





	1. Lusamine

**Author's Note:**

> How the hell I came up with this near the END of MILF May will vex me forever, but for now, just enjoy more Pokemoms getting down and dirty in the lap of luxury. Welcome to the Hano Grand, and the very special accomodation- the Nidoqueen Package

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

Trading the ol’ Skulls for a monkey suit wasn’t really his plan, but after the gang broke up he wound up with a sweet gig. All it cost was his hair and pride, but what’s pride in the face of a few hundred pokedollars...an  _ hour. _

_ Clack Clack Clack _

“Ah, there you are!”

He turned to the woman approaching him and froze. Lusamine - absentee president of the Aether Foundation. Therapy had done her well, and she looked quite good given the harrowing ordeal a few years back. He knew she was a rather generous contributor to the hotel, but didn’t expect to see her in person. He tried not to scramble to his feet and instead look composed.

She paused in front of him, eying his uniform with a calculating eye. A pondering finger wound up around her chin as she cradled her elbow. “Hmm, you seem familiar...ah well, I’m sure its nothing.”

Despite her nonchalant dismissal, he was still drawn to her. Sure he knew that she’d been a touch insane...didn’t matter, she was still pretty hot.

She snapped her finger in sudden realization. “Ah, where are my manners. I’m Lusamine - the benefactor of your project.”

He looked at her hand before matching her handshake. Her soft, supple hands felt like cream in his palm. “I’m ah...Gray. Nice to meet you, miss”

Lusamine’s eye flew up before she laughed. Her melodious voice carried a concerning tinge to it - like a violin string just a little too tight and ready to snap. “A ha ha! Ahhh... I haven’t been called ‘miss’ in quite a few years…”

Oh right - she wasn’t just crazy hot, she was also a mother. The unholy trifecta.

Lusamine took his meager trespass with good humor. She leaned in, showing a coy side beyond her previous professionalism. “Well thank you for the compliment,  _ Mister  _ Gray. First time in the Hano Grand?”

Gray nodded, staring around the opulent lobby. “Yeah. It’s a bit...quiet.”

“Oh don’t worry - it’ll be busy soon enough. The staff are mostly out enjoying the island before they get ready for the season. You’ll have time to meet them all before then. Until then, please take a seat.”

He obeyed and sat back in the chair. She sat down across from him, sinking into the plush couch. Her leg crossed over, followed by her hands on her knee. Professionalism oozed off her, mingling with the crazy, the hot, and the motherhood.  _ ‘I’m in danger…’ _

“So let’s get down to business - you’re not  _ technically _ employed by the hotel, but you are part of a special program for an exclusive group of guests.” She went over the details that he’d already known about. It was pretty much the first thing he’d been told before he went in for his physical.

Gray nodded, trying his best to act like the man who already earned the job. “So what’s the particulars?”

Lusamine hummed, still staring at him. He could just barely see her other eye from within her extravagant hair, but something in the way it was gazing at him sent a shiver up his nape.

She finally made a move, rising up from the couch. “Actually come with me...we need to evaluate your performance first.”

Gray stood up as well, trying to ignore the way her breasts were swaying. He followed her, watching the way her ass bounced beneath her skirt. Her long, sensuous legs seemed to stretch forever as she led him to the concierge’s desk. “This should do - I need to be sure you’re the right man for the job.”

She stepped behind the desk, motioning him to join her. Gray tugged at his collar, feeling her predatory gleam following his bald head. “What, like a test?”

Lusamine dispensed with the formalities and simply grabbed his shoulder. The shapely mother turned him around before getting Way too close for any HR rep to brush off. Her plump, fuckable lips curled into a devious smile.

“Something like that~”

* * *

_ PAP PAP PAP PAP PAP _

Wet, scandalous slaps echoed through the silent lobby. The soft babbling of fountains were drowned out by the echoes of moans and delighted gasps. They were already at it, right in the middle of the lobby in full, brazen view of the glass doors.

Lusamine cooed, squirming in his grasp. Her hips rolled and gyrated against him as he sawed her moist, hot twat. Supple skin rocked with every thrust, sending sweat flying. “ _ Oooooh,  _ that’s it~”

She’d stripped down to nothing, leaving her hot black panties askew and happily stuffed by a nice, fat cock. A thick, unshaved bush of blonde pubes were already drenched in sweat and sin. Her legs dangled over the edge of the concierge desk, smacking her ankles against the side. Sharp nails scraped against the polished edges, hiding little cracks beneath the surface.

Gray kept thrusting and relished her tight snatch. Nothing - not one of the hot tails back in Team Skull, could possibly compare to a MILF. somehow she felt even better than an eager virgin.  _ ‘Must be...t-the experience.’  _ He grit his teeth. “F-Fuck! H-How are you this tight?!”

Lusamine glanced up between her swaying hair. Her carnal smile morphed into something impish...and vaguely sinister. She pushed herself up and shoved her bare breasts against his chest. Their eyes locked….followed by her legs around his waist.

“Heh heh, t-that’s for me-eee to know...and you to  _ never _ as-ssss-k.”

She pushed down, fully hilting him in her pussy. _ “Ooooh~” _

_ “Shhhhiiit!” _

Gray’s curse brought her to fits, giggling like a twisted schoolgirl despite the lascivious nature of their antics. She pulled him back until he was almost over her. His toes screamed in his shoes as he struggled for balance. “Now keep going - your evaluation isn’t over yet~”

He struggled to keep thrusting, hindered by her thighs on his ass and her nails now grazing over his back. The crisp, silk shirt kept her from breaking skin, but he still felt little daggers poking his skin. But it was her sultry, slightly unhinged smile that really got his hips slapping

“H-Hah..Y-You really want thiiiis, don’t you?” she growled with want practically oozing out of her lips. Drool trailed down her chin from between her bared teeth. She looked like a feral beast - eager to be bred by some lowly punk playing posh.

Gray fought the urge to cum, desperate to last at least long enough to give her an explosive finish first. “D-Damn right I do!” 

“P-Perfect! OHHHH! Y-YOU’RE HIIIIIIIIIIIIIIIIIIII-IIIIEEEEEEEYAAAH!”

Lusamine’s back smashed against the desk, taking the wind out of her lungs. She didn’t even feel the pain, not compared to the orgasmic firestorm consuming her body and burning out her nerves. A shrill, piercing cry cut the serene lobby.

Gray collapsed on top of her as he unleashed a weeks worth of pent-up lust. His intent to be as professional as possible for the job wound up in his benefactor’s favor as she was stuffed with hot, syrupy cum.

She cradled him like a babe, relishing the cool breath over her boob. Her sweaty thighs squeezed against his buttocks and kept him plugged in her twat. Lusamine’s nails traced against his sweaty, covered back. She reached up and cooed in his ear, “Oh yesss...I think you’ll do nicely.”

Her thighs unlocked, letting Gray stumble back out of her pussy. His back hit the wall as he gasped for breath. The shapely ex-president simply hopped off the desk and stand and pose over him. Hand on her hip, towering over him on her stiletto heels. She looked imposing, radiant….and absolutely goddamn  _ hot _ .

Lusamine walked away with telltale clacks, leaving her discarded dress behind and not even caring if she was dripping onto the floor. Her hips rolled with every strut, pushing out her bare, fat ass hugged by fine black panties. Gray snapped out of his stupor long enough to grab her effects and hobble over to her at the elevator.

She turned to him, once again with that impish smirk.“Why don’t we go discuss the particulars,  _ Mister. _ Gray?”

_ Ding! _

“Please, step into my office~”

* * *

_ ‘Her’ _ office was just a simple stateroom - one of the smaller ones off to the side of the hotel. The bed remained immaculate and untouched as she led him over to a black lounging couch. He looked at her, reclined along the couch with a single arm on her upraised knee.

Gray was down to his socks now, cock hard and ready again. He drank in the sinful yet heavenly sight of a ripe MILF baring all before him. “So is this my casting call?”

Lusamine laughed at the pathetic farce. “That should be obvious...” she gave her ass an inviting smack before spreading her legs wide open.

Gray quickly joined her on the couch and spooned behind her, letting his pulsing cock rub against her slick pussy. His hands snaked around to cup her heaving breasts. Lusamine reached down and used her nails to guide him into place at her inviting core. It took a few tries, but he finally got into her with one abrupt thrust.

The MILF sighed, relishing the feeling of fullness that she’d already been missing. Her hips rolled back until he was nice and deep in her velvet cave. She looked back with a strikingly serious glint in her eye.

“Now listen closely, mister Gray. There’s going to be a very lovely selection of women staying here, and they’ve pulled some strings to have an  _ all-inclusive _ package here at the resort - yours.”

Gray choked back his shock. Even with this tryst, he hadn’t considered that there would be something  _ more  _ to this arrangement.  _ ‘On the other hand...I guess that’s why it's called the Nidoqueen Package.’ _

Lusamine started rolling against him, gently pushing and pulling against his cock. “You will cater to their every whim - their every desire, no matter when, where, or what it is.”

Gray listened on, already excited for what the next two weeks would offer him. He reached below and pulled up her thigh for better access. She mewled but quickly kept going with shocking restraint. “If a woman wants you to join her for dinner at the restaurant, I expect you in your best. And if she decides for a meal under the table, you better have a world-class poker face.”

“If they want you to join them in the jacuzzi, you will happily drop what you’re doing and join them. If they want to get fucked in the ass at hole 18...you better be ready to drop your pants and get to thrusting. Understood?”

Lusamine paused long enough to reach back and grab his cheek. Without prompting, the two came together in a shockingly searing kiss. Whatever restraint kept their loins at bay was no factor for their hungry, passionate lips.

Her tongue invaded his mouth and quickly wrapped around his own tongue. Gray was once again reminded of what kind of woman he was now in the employ of. A MILF who had no restraints about getting freaky, with or without sheets.

_ ‘I think I’m gonna like this job…’ _

She pulled back, eye dazed and spit lingering between them. Lusamine shook off her stupor before continuing on like nothing had happened. “Basically, anything that they want from you within the confines of the hotel is your whim.”

Against his best interests, Gray asked a question that had lingered ever since he carried her discarded dress behind her. “What about...the mess?”

Once more with that smirk - the one that offered pleasure with just the right does of pain. “Don’t worry about that - it’ll be clean before anyone can even raise a complaint. All you have to focus on is being a good servant for my guest...understood?”

“Yes, ma’am.”

“Good, now let’s discuss benefits.”

Lusamine reached back for his shoulder and pulled him atop her, still plugged up. She landed on her stomach and boobs before being pushed further in by the man on her back. Her hands reached out and gripped the edge of the couch. The two resumed in their new position as she kept going. “Y-You’ll get a bonus for every experience that’s marked p-positiveeee. D-Double for groups.”

Gray’s cock throbbed at the notion. Not just one sultry, inviting MILF, but  _ two _ ...maybe more.  _ ‘And I’m getting paid for all this? ...wait, does that make me a man-whore?’ _

_ “OOOOH,  _ r-right there~”

_ ‘Fuck it - I’m gonna be a man-whore!’ _

With that brief crisis behind him, he decided to get a bit friskier with his new boss. He reached for her arms and pulled them behind her back. Lusamine arched her back, but kept going as best she could.

“G-Guest can have up to two s-shessions a day, T-Twenty five minutes per session.” she paused long enough to shake away the spit from her mouth. “You’ll be requ-uuuuuh-red to make yourself presentable before the next one.”

He leaned in, invading her intimate space, and hissed in her ear. “What if they  _ like _ the smell? The stains?” he punctuate his question by tonguing her mercifully clean ear.

Lusamine’s back shuddered, sending goosebumps all over her bare, sweaty body. She instinctively bucked back, trying to match his feverous pace. “T-That’s to their discretion. Y-you must be clean to the rest of the sta-aaaaaaaaaaaa-f-f-fuck!”

Gray’s thrusts grew forced as he struggled against her locked-down snatch. Her body thrashed and buckled, sending sweat everywhere. Quim stained the seat beneath them, drenching the once-sterile black cushion. “GODSHH YOU-?!”

He hooked two fingers into her cheek, keeping her mouth open. Her orgasmic screech came out gargled as spit flew out. Her hard nipples scraped against the couch with every skin-slap.

Eventually her scream lowered to a moan and then dwindled to a whimper. Gray released her and let her head hit the cushion. He pulled back and smugly asked. “S-So am I qualified for the job? When do I S-Shit-art?”

The MILF’s arms blindly groped beside her before she finally found ground. Slowly, she raised herself up until her breasts were free to sway and slap in the air. Her voice made him pause, if only for how...serene, it sounded.

She didn’t sound like a woman who’d been fucked to climax...she sounded like  _ she _ was the one in charge. “Oh you’ve already more than shown that...but you still have to sign your contract.”

Lusamine pushed him off and almost made him topple off the couch. He quickly got the gist and scrambled around to the side facing her head. She rolled over, presenting her bare front in all its brazen glory. Her lips pulled apart as her tongue lulled out. “Now get that hot ink ready, and sign all over me~”

Gray pumped his angry dick, eyes locked on her squirming, sweat-slick body. Her breasts, her hips, her sopping wet twat...but it was once again her lusty eyes and slightly tweaked grin that set him off.

The shower he gave her clung to her skin and utterly tarnished the brand new couch...

* * *

Lusamine pulled an employee’s badge out the envelope and waved it at him. “Okay, so this will get you into any room of the facility, regardless of credentials. The rest of the staff know what this does, but don’t know what _ your _ role entails...so keep it that way.”

He had a hard time staring at the platinum-lined badge, especially as the philanthropic MILF was strutting around  _ his _ suite in a tiny bathrobe. She hadn’t even bothered with a shower and smelled every bit like the back-alley whore she looked. He could still see the stains dripping down her thighs, especially after they’d walked across the whole of the hotel with her practically naked.

Lusamine flicked the plastic card at him, smirking as it smacked him in the face. She turned around and bent down, exposing her sore rump. He watched her hips roll as she fished for the next of his toys.

“And THIS is your Xtransceiver - any women who’s part of the program has a similar model that they can tap into at will and contact you. Be sure to set yourself to busy if you’re preoccupied, or you WILL be docked pay for not responding.”

Lusamine slapped the watch-like device in his palm. He eyed it with keen interest, marveling the sleek tech. He’d never be able to afford something like this back in the gang...well he didn’t really  _ afford _ anything back then.

She took the opportunity to slink around him and push her swollen breasts into his back. Her lithe fingers wrapped the Xtransceiver around his wrist, dragging her nails across his bare arm. A single finger poked the side and brought out the secondary screen. The main face blinked to life, showing the two of them.

“It has a camera and a video recorder - what you choose to do with it is your business, but I trust you won’t be compromising the sanctity of your contract, right?”

She emphasized her statement by pushing into his back just as she snapped a picture. He got a good, high definition picture of the Aether President, saved right into the device.

Lusamine nodded in approval and slipped off his back. “And that should be it - as you can see, your suite is stocked with supplements and a full bar. You clock in at 5am, have one hour for lunch, four breaks of no more than 15 minutes a piece, and clock out by 8pm. After that you’re free to enjoy the facilities or indulge in more time with our special guests. Any questions?”

He glanced up from her lascivious picture and decided to push his luck. “Yeah...care to join me testing out the bed?”

Lusamine grinned, showing more of that wild streak that’d made him weak in the knees. Her hands traced up her hips to the belt around her bathrobe.

“I thought you’d never ask. I think you’re going to work out well here~”

  
  



	2. Ginki

**Notes for the Chapter:**

> well since she doesn't have a name, had to get a bit creative with it. hope you all enjoy :)

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

_Bzzzt_

Gray flicked off his Xtransceiver as he rushed to the signal. He kept his pace brisk but professional as he weaved past groups of chattering tourists and guests. His focus was on the source of the signal on the opposite end of the lobby.

He cleared the atrium and rounded the corner to see a perky looking woman waiting by the ladies’ room.

Ginki of the Johto region, Champion Gold’s mother. An absurdly young looking woman who filled out her new white sundress nicely, showing off her wide hips and a hint of her modest bust. Her hair was done up in a pair of loosely coiled loops, with only a fringe free to pop over the edge of her bandanna. A pair of sandals and a winning smile completed her ensemble...well all that and the powder blue Xtransceiver-Slim on her wrist.

She perked up at his presence and offered a polite bow. “Hello! You must be Gray - it’s a pleasure to meet you.”

He offered his own bow in response. “The pleasure is mine, Ms. Ginki. How can I be of service?”

His tone was polite with just a slight tinge of submission, just like she’d told him. Lusamine had drilled it in his head as he’d plowed her ass - treat each of her guests with respect and call them ‘Ms.’ unless they said otherwise.

Ginki glanced at the restroom door. “I think there’s something in the ladies’ room. Could you check for me?”

“Of course,” Gray walked in and quickly placed a ‘do not enter’ sign outside. He inspected the interior, right down to each of the stalls. _‘Be meticulous, down to every last inch.’_

It looked...pretty much exactly like a hotel’s restroom should. Opulent, polished, and with a stupidly expensive soap on the wall. He turned around and declared, “Ms. Ginki, I’m afraid there’s nothing in...here?”

He hadn’t heard Ginki enter behind him, nor expected her devious smirk. She leaned in, barely even coming up to his chin but still trying to exude confidence and control. Gray noticed that one of her dresses sleeves had drooped off, exposing a bare shoulder.

He resisted the urge, the craving to simply jump her ripe, mature bones. Lusamine’s warnings hammered in his head, all the way to the last thing she’d said before they greeted their guests. Her very last rule - make no moves until they said the password. His codename, reserved only for the women involved in this little club.

Giniki leaned in, caressing his stiff silk vest. Her lips oozed out, “There is now, _Nidorino_ ~”

* * *

_Sclick sclick schlick_

Gray’s knuckles dug into the MILF’s hips as she bounced atop his cock. Her sundress drooped over her bra-clad breasts. Her drenched panties dangled around her feet as sandals knocked against her soles.

Ginki leaned back until she was pressed against his dress shirt. She reached around and grabbed his nape for support. “O-oooh...y-you’re just as good as they promised. And s-soo big~”

He said nothing and merely focused on railing her soaking twat. His Xtransceiver finally dimmed after he barely managed to switch his status to ‘occupied’ before she shoved him into the stall. Johto manners had flown clean out the window for the lusty MILF, alongside the veneer of stately decorum.

Gray marveled at how different she was from Lusamine - how light and limber Ginki was. He wasn’t really sure if she was older or younger than the ex-president, but it didn’t really matter to him. _‘Besides, that was one of the big no-nos that she hissed out between deep sucks.’_

“Hah, haaaah - p-pull up my legs,” she insisted. He obliged by directing his hands to her thighs and hiking them up. Her sandals barely hung from her toes as she kept thrusting against his crotch. “J-Just like that, yessssssss~”

Ginki reached up for her bra and cupped her breast. She pulled down the side with her thumb, exposing an erect nipple to play with. Her other hand reached between her legs and fiddled with her swollen clit.

“Can you believe that creep was dressed as a Machamp?? Who _does_ that?”

A guest’s complaints made the two freeze in place. Neither one had actually heard the door open...the door that _should_ have been closed with a little sign warding off guests while Gray was inside. Even before he’d been roped into entertaining his guest.

Ginki glanced back between her disheveled bangs One look at her oddly shining eyes made it clear what had happened. He could almost hear her excuse - how she may have ‘accidentally’ knocked off the sign as she snuck in behind him. And from the way she was rolling her hips, it was clear that she wasn’t planning to stop now either

“Guess we’ll just have to carry our own bags to the kart...man, what a pain.”

The two golfer’s comments passed over his bald head as he fought back the impish MILF. Her shapely hips rolled against his lap. It could barely be heard, but for their ears it might as well be a monsoon.

Ginki was the only one that was actually trying to keep up their rhythm since Gray was frozen in abject fear. _‘Crap! I know the boss said I might wind up in a scenario like this...but still!’_

She was far less reserved about doing all this - it _was_ her goal after all. She wanted to use this once-in-a-lifetime vacation to cast off the strict teachings of Johto and just be a crazy, horny tourist. She already felt her libido spiking over at the thrill of being fucked, especially so close to total strangers in the fancy hotel’s public washroom.

Neither one dared to glance at the countdown on their Xtranscivers as her session dwindled down. Abject fear kept him from cumming in her adrenaline-clenched snatch as the two golfers took forever to apply needless makeup. Finally, They heard the door creek open, finally causing her to elicit a subdued moan.

_‘mmm-mmph?’_

“Hmm?”

Ginki had the decency to bite her lip before glancing back with an apologetic pout. Gray didn’t remove his palm, not really trusting her anymore. He nervously glanced at the thin slit leading outside, watching the growing shadow as the woman crept closer...

“Hey, let’s go! Tee-times’ in five minutes and I’m _not_ gonna miss it again!”

The other golfer sighed and shook her head. “Must’ve been the vent,” she chuckled before calling back. “Yeah, I’m coming!”

_‘So am I!’_

As soon as the door swung shut, Ginki cut loose. She gripped the sides of the stall, using her new leverage to smash down on his throbbing cock. Her hair was bouncing and shaking itself loose, nearly coming free of her headband. Gray’s fists returned to her hips as he tried to keep her atop him all the way up to the threshold.

“F-Fuck!”

She didn’t hear him as her world turned white. Pure, rich fire burned her to the core as she greedily accepted rope after rope of potent seed. Her juices gushed out from her stuffed twat, splashing against the tile floor.

Spent, he leaned back against his chest and sucked down desperate gulps of air. Gray got a good whiff of her fragrant perfume, as well as the salty tinge of sweat from their vigorous passion. “ _huff...huff..._ O-Oh wow...she really really wasn’t kidding about how all-inclusive your package is...”

_Brrp. Brrp._

Their Xtrancivers buzzed in tandem, signifying the end of their session together. She glanced down at the slurry pouring out of her snatch and how it almost hit the toilet bowl.

Almost.

“Looks like we left a mess.”

“Mmmhmm,” Gray agreed as he flicked the request for ‘cleaners’. They’d likely have better luck of keeping the room off limits as the finished wiping away the evidence. He should also have just enough time to get to the downstairs laundry room and change into something presentable.

Ginki ignored whatever he was doing and simply rose off his lap, showing off the way his spunk bubbled and drizzled out of her spent snatch. He got a good eye at her shapely hips beneath the sundress, especially her tight butt. She looked back with another smile and raised her wrist to show off her Xtransceiver’s screen.

_Daily Sessions remaining - 1_

“Mind taking me to my room, Nidorino?”

* * *

The Nidoqueen Package had rented out an entire floor full of suites on the private floor. Not counting his own accommodations on the opposite side of the hotel, there were 13 occupied rooms out of a total of 15. The other two were free to use as ‘rest stops’ between his duties. Each suite was filled with all the accommodations that a paying guest would want, from a kitchen to a balcony-

“OOOOOOH, YEESSSS!”

...And soundproof walls.

Her dress was tossed aside, alongside his suit pieces. Ginki was once again bouncing atop him as he sat on a much more comfortable seat, facing him this time. She squeezed his calves against his thighs, enjoying the friction between their dry flesh. Her palms dug into his shoulders as he bucked up into her scorching hot crotch.

“Y-You’re sooo good - I-I need more!”

Gray obliged her request, now that they were in ‘safe’ grounds. He reached around and smacked her ass. “ _Eeep! O-oooooh~”_

Her fingers reached for the headrest and clung for dear life. Wet slaps echoed through her suite, bouncing off the walls and thundering in their ears. She felt his balls smacking against her ass, making her squeak with every clap.

Gray reached up and sucked down on one of her flaying nipples. Ginki’s nails dug into the chair. Her wanton smacks morphed into sensuous rolls. She felt him grinding against new, deprived spots in her twat and showed her appreciation. _Yeeeeeessss~”_

He reached for her other breast and started pinching her other nipple. His palm squeezed her modest tit and kneaded it like a nice ball of dough. He followed her rhythm, enjoying the slow but deep undulations between them.

If either one cared to look, they’d have seen a fantastic sunrise. The main rooms of the Nidoqueen Package all faced the ocean, giving them an unrivaled view of the dawn. Such a luxury would be wasted this precious morning as the champion’s mother indulged in her son’s prized winnings. _‘Thanks for the birthday gift, honey~’_

Gray didn’t need to know the source of Ginki’s exclusive privilege, the same way he didn’t need to know about _any_ of their means. To him all that mattered was a coo of his codename and he was down to fuck - wherever, and however, they wanted.

Their sweat mixed together between sore skin. Her chair was already stained by sin and shame. She’d insist on keeping it, at least for the duration of her stay. _‘It’s my favorite seat, and it comes with such a nice pillow to boot~’_

He alternated between her breasts, tending to them with unmatched professionalism. Each lick, each tweak, each thrust - it all made her toes curl as she straddled the younger man, as well as the edge of no return.

But then her clit scraped against his shaft, and she took him right into the void.

“Ah, ahhh, ahhh, A=AAAAAAAAAAAHHHH!”

Gray fell back, limp. His screaming muscles somehow reached through the orgasmic storm. His vision exploded into stars as his final thought rang in his head _‘I love this job!’_

She collapsed in his arms, curled up as he pumped even more thick jizz in her stuffed womb. His head tilted back as he basked in the after-sex bliss. Her nail drooped down and lazily traced his bare chest. _‘This is more like it…’_

_Brrt. Brrrt._

The two groaned at his alarm, neither one willing to get up. Ginki looked at him with that infectious smile. Her hair ribbons drooped down her sweaty shoulders as she panted for breath. “Y-You do room service right? Early Morning?”

  
  



	3. Grace

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

_ “Hee….hooo. Clack. Hee….hooo. Clack.” _

The usually bustling gym was practically dead as Gray stepped in. The Hano Grand only had a modest fitness center, but it offered an unrivaled view of the eastern beach - perfect for working out as the sun rose. 

But it was still dark out, with only the slightest hint of light coming from the horizon. Gray wasn’t fazed however. It had only been a few days, but he could already guess who was there before he even saw her bouncing tits or full ass.

Grace, former Rhyorn racing champion of Kalos. A celebrity in her own right before her daughter, and one that took her retirement in stride. While she’d long since given up on racing herself, her body was still in keen shape in order to rear a new generation of riders. Her curvaceous figure was covered in nice, toned muscles- ready to grapple and grasp atop a thundering Rhyhorn. The sweat on her slick skin and the tight white exercise top and navy yoga pants only compounded her ripened beauty.

_ “Haaaaah… Clack. _

The ex-skull  _ felt _ the weights coming to rest. Somehow the MILF from Kalos was pumping iron that put the bulk of his old gang to shame. Even then he couldn’t think of a single member that could cut a figure like her. 

Grace wiped the sweat off her brow before she turned to face him. She noticeably perked up once she saw he was there and offered him a wide smile. “Oh hey, kid! Just finishing up.”

“Good morning, Grace. I have your towel and water.” He handed her said implements. The MILF took them gladly, wrapping the towel around her sweaty neck. “Ahhh, just what the nurse ordered. Thanks, hun.”

She popped open the bottle and splashed her forehead, letting the cold water settle in her matted hair. Gray noticed several drops land between her breasts and on her damp top, showing a little of her training bra beneath it.  _ ‘Damn...how the hell are they so perky?’ _

Grace chugged down the rest of the bottle, ignorant to his staring. “ _ Ahhh,  _ that hit the spot. Nice to be able to work out without people getting in the way here.”

She looked outside at the still-dark sky. “...Guess it helps waking up early, huh?”

Gray nodded in agreement. “I’m sure. No one really starts using the gym until the sun’s already up”

His innocuous admission made her perk up. “Oh….is that so?”

He didn’t miss the way her voice had pitched down, but played it coy with a charming smile. “Yes...you shouldn’t expect anyone for another hour, maybe more.”

Grace’s smile matched his, along with her fluttering eyes. Her finger reached up and tugged the collar of her top. “Is that so…Well I  _ was _ gonna do a light jog around the beach.  _ Buuut, _ if I’ve still got the gym to myself, why not do another set?

“I’m gonna need a spotter this time though.

“I’m not sure how I can help you, Ms. Grace.”

“Oh don’t worry, just doing some simple exercises is all.”

She flicked on her Xtransciver and fiddled with the buttons. Gray felt his own model buzz on his wrist, already knowing that her reservation had been confirmed. The MILF mounted the bench and stretched out her rippling back. She glanced back at him with an inviting smirk.

“Now let’s get started,  _ Nidorino _ .”

* * *

“We have to start off light, do all the reps. Nothing to heavy yet, got it?”

Gray grunted in agreement as his hands grabbed her shapely hips. His cock pistoned in and out of her moist twat. He had the lovely sight of her full ass rippling against his crotch between her tight rhyhorn hide-printed panties.  _ ‘Well if they make Growithe prints, guess that only makes sense.’ _

Grace cooed before returning to her lifts. Her top was bunched up with her pants, leaving her matching rhyhorn bra straining against her bouncing breasts. “Slow down - we’re keeping this nice and even, it's a jog, not a sprint.”

He found it hard to obey, but ultimately obliged. His employer’s words rang in his ear.  _ ‘Treat them like queens - every word is law.’  _ If Grace wanted to go slow, he’d go slow...reluctantly.

The MILF kept lifting even as her hips rolled against his dick. She barely had any weights attached, but it was enough to give her just a little resistance pulling down. Not as much resistance as her velvet walls, but enough.

“Ahhh...G-Go a little harder, but not faster. Got it?”

Gray obliged gladly, anything to increase the pace. He took the chance to reach up and cup her breasts. “H-aah! L-Like them, don’t you?”

His answer was to pull down her bra and let her rocky puppies free. Gray marveled at how firm her boobs were - large enough to have some jiggle, but not big enough to start sagging. Even if Grace didn’t have a nicely toned back, she’d probably be able to live with this nicely formed rack.

Their motions fell into synch - pull down the bar, pull up her tits. She breathes in, he thrusts out. A nice, subdued slapping passed through the modest gym. The rising sun started to peak out from the ocean’s waves.

She turned back to him after several full sets. Her already sweaty body was practically glowing in the early morning light. “Why don’t we switch? You could probably use a little arm action yourself, right?”

Gray paused as he tried to shift around until he was sitting where she had been. He reached for the bar, only for her to stop him. “Before you start - hold onto me.”

Grace arched back, taking her legs with her. Gray managed to catch her thighs before she wound up slipping off his dick and gave her time to catch herself on the floor. Then she slowly turned, rolling her ass and stretching herself out until she was facing up. She looked back to him with a wink, offering her outstretched breasts a little shake to tease him further. The MILF curled herself up with her impressive core until they were once again face to face.

“W-Wow.”

She grinned at his shock. Her arms wrapped around his neck before she gave his nose a little flick. “Don’t just sit there - you’ve got reps to do~”

Gray nodded before pulling the bar down. He nearly smacked his head with the bar.  _ ‘Nice to see I haven't gotten soft…’ _

Grace watched him a few times before she began grinding down his cock. Her feet planted on the ground and let her toned thighs do all the lifting. Lithe, woven arms slid down his neck until she was grasping his shoulders. “T-That’s it...niiiice and even.”

She kept riding him, even when he paused between sets. Her thrusts acted as a metronome to pick up on - slowing down when he was getting out of synch. Her vice-like grip on his cock wore him down, and eventually he reached his limit.

“G-Grace, I’m-”

The MILF swiftly dismounted him and shoved her mouth over his cock. The brief loss of her tight snatch before her mouth gobbled him up was all he needed before he exploded. Salty cum filled her cheeks and nearly choked her outright. It took constant swallows to keep her from drowning in spunk.

Gray’s back hit the bench as he gasped for breath. Maybe it wasn’t the most intese workout he’d ever had, but the addition of sex had certainly made for a unique experience.

Grace’s attempts to swallow faltered as she pulled him free. A few weak spurts hit her face, making her wince. Her cheeks stayed billowed out as she struggled to deal with the loads already stuffed in her mouth.

At last he finished, slumping over as adrenaline left him. The MILF focused on slurping down as much as she could before scooping up her small facial and dipping her sticky fingers between her lips. Her jaw opened wide, showing her cum-soaked mouth before she swallowed the last of it. “Nicsh wohk- _ ulp _ ...Nice work.”

Gray could only grunt, much to her bemusement. She reached for her discarded top and wiped her face clean of the marks of sin. He just sat there, trying to recover, as she pulled her yoga pants back on and wrapped the towel around her neck. One last-minute adjustment to fix her bra made it look like she’d merely had an extra-strenuous session at the gym. 

Partially true.

“I think that’s enough working out. Mind escorting a lady back to her room?”

* * *

“Aaah~!”

Grace was pressed against the glass with a delighted yelp. Her tight black shirt pushed against the window, showing the nubs of her nipples. Her hastily applied panties were already askew and smearing against the pane. Her tight asscheeks were pushed asiide by his thick girth.

“Ooooh...e-enough games, Nidorino. It’s time to ride~”

Gray smirked at her cheesy lines, but certainly agreed with her. He recalled a certain suggestion from his boss out of the list of ‘safe’ phrases that could be used to escalate their sessions. He leaned in, letting his hot breath assault her ear. “Do you like it...dirty, Ms. Grace?”

The MILF bit her lips and tried to hide her blush. The thought was certainly enticing...but even a champion rider like her had limits of comfort. “N-No...I can’t say I do.”

He frowned, but wouldn’t push her any further. He kept his tone polite and welcoming, masking his disappointment. “Very well - shall we begin?”

Grace lifted off the glass long enough to pull up her shirt. Her bare, perky breasts were smooshed against the glass, sending delighted chills up her spine. Her fist pulled his bare head into her eager lips. “Damn right.”

The kiss they shared was sloppy and heavy, with tongues battling within their hollowed cheeks. Gray reached forward and palmed her tit, kneading it like a fine roll of dough. Their free hands reached down and shakily guided him back into her waiting twat.

_ Pap pap pap pap pap _

He started rough right out of the gate, pounding in her eager pussy with the same force of her beloved Ryhorns. Her hips eagelry smacked back against him. Arousal gushed out of her stuffed loins and smeared her thighs.

Grace was panting, already feeling more of a burn from a few minutes of window pounding than the whole of their earlier ‘workout’. But it wasn’t enough - not yet. “R-Rougher - I want you to  _ ride _ me, kid!”

He blinked at her brazen snarl, but was more than ready to accommodate her. His hands left her hips in favor of the glass door. The wet slaps of hips grew louder until it was almost deafening.

“Ah, oooh, oh  _ f-fuck _ that’s iiiit!”

Grace’s head dipped down to catch the rim of her top before her shirt fell back down. Spit soaked her shirt as her screams were muffled. He took that as an excuse to go even further on her.

Gray’s arms hooked around her shoulders and locked down behind her neck. Her nails scratched against the glass over her head. Her teeth threatened to tear a hole in her shirt. “ _ Muh...Muh cuhing!” _

Her pussy clamped down on him as she buckled and thrashed in his grip. He tried to thrust through her orgasmic seizures, but simply found it impossible to resist. “Grace I’m-”

Words were lost in addled babbles as climactic fire burned them alive. Hot, syrupy cum blasted into her waiting womb. Her tight snatch ensured that every drop would cross the finish line and swim in her mature, fertile sex.

Gray’s grip relaxed and let her fall forward with a  _ thud. _ Grace sighed as she felt the nice, cool glass on her cheek. She turned back to him with a satisfied, sweaty grin. “Kid... you really know how to treat a lady right, don’t you?”


	4. Johanna

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

Gray audibly grumbled as he filled up the towels. The heat from the nearby sauna was getting to him, making his suit stick to his sweaty body. Out of all the crazy things the Hano Grand had, he found the sauna to be the most pointless, regardless of a novel’s worth of health benefits.  _ ‘Want to sweat it out? It’s called going outside!’ _

He was so preoccupied in his thoughts that the door almost crashed into him as it swung open.

“Need to grab a fres-AHHH?!”

Johanna - Legendary Coordinator from Sinnoh. While her star had long since dimmed in the wake of her daughters, she was far from forgotten. After accumulating all her savings from her career, she’d only needed a minor kick from her daughter’s own coffers to secure her place in the Nidoqueen Package. So now she had two straight weeks in a tropical paradise to flaunt and frolic her mature body as much as she pleased.

Her short, full hair was wrapped up in a towel, but he could just make out the telltale red clip above her left brow. Her shapely body was covered in a similar towel, one that hugged her hips and framed her bust quite nicely. Her feet were bare, letting him see the culmination of a world-class pedicare.

She gasped at the sudden intruder, but quickly relaxed once she recognized him, replacing her shock with an apologetic smile. “Oh! You’re the nice young man that took up my luggage. Sorry about that - I thought I was alone.”

An understandable justification, with the bulk of the hotel being out on the beach to enjoy the nightly luau. “It’s no concern, Ms. Johanna - I’ll be out of your hair shortly.”

Oh please, just Johanna is fine,” she insisted. Her warm smile turned a bit more  _ heated _ as he eyes lidded. The words that cooed out sounded more silken, more inviting. “You’re working so hard. Do you have time to join me for a nice steam?”

His lunch break was scheduled for five minutes, and as much as the idea of stripping down next to the drop-dead gorgeous MILF appealed to him...he just really didn’t want to deal with the heat anymore.

Gray ultimately shook his head and apologetically explained, “I appreciate the offer Ms. Jo...haaaaah”

Johanna had moved next to him, letting her towel drop. Her supple, shapely body in all its glory, with just the right amount of sweat to make her shine in the inviting light. He brazenly stared at her bouncing breasts as she reached for her belongings in the adjacent locker. She’d pulled out her Xtransciver and flicked over to ‘reserve’ him. 

“Are you sure you don’t want to join me...Nidorino?”

* * *

Gray’s naked back pressed into the wooden bench. The serrated boards were digging into him, but not to such a degree that he felt pain. Instead his sweaty, bare body was simply splayed out in the steamy sauna. He was caught somewhere between the heat on his skin and the one wrapped around his loins as his MILF guest undulated atop him.

Johanna had ultimately convinced him by offering to let him lay down as she rode him. She chose to go slow, sensuous - more like an intimate crotch massage than a lascivious romp. The thin, dark patch of pubes seemed to lead him in and out of her loins. 

Still, despite the pleasant feeling stretching out her walls, a frown was planted on the Sinnoh woman’s lips. “Wow...y-you’re so tense. They’re working you ragged, aren’t they?”

He tried to stay composed and pass off her worries. “I-it’s nothing to be concerned about, Johanna.”

The MILF wasn’t convinced, and simply prodded his straining muscles. The pressure made him yelp in pain, like she suspected.. “These don’t feel like nothing to me, honey. Trust me, I know what it's like to work yourself to the bone.”

Her hips paused, keeping his dick in her nice tight snatch. Johanna’s palms lightly squeezed his shoulders as she probed the many, many knots. She offered him a reassuring smile that shines brighter than her sweat-slicked skin. Just let me do my thing, and you lay back and enjoy.”

She resumed her pace, gentle and caressing. Her fingers kneaded and rolled his shoulders, finding every possible kink she could reach. “There we go...isn’t that better?”

Gray moaned at her touch. He had to admit that she was spot-on in her assessment, and her solution. “Oooh geez...t-this feels so good J-Johanna…”

Her giggle sounded far more husky and sensuous for his addled mind. “I could always give you some pointers, and give you some  _ practical _ examples.”

She emphasized her suggestions with a few hip wiggles. Her tits bounced between her shoulders, nearly hypnotizing him. Gray reached up to grope her wrists.  _ ‘Wow, she feels so...so smooth.’ _

Johanna felt his hands on her arms and smiled down on him. She raised her hands and cupped her boobs, giving them a few temptuous shakes. “You can touch them if you like - work out your stress on me.”

He took her offer, and they exchanged hands again. Johanna caressed and tweaked his shoulders, as Gray started rolling and kneading her fantastic breasts. He gave her puffy nipple a little tweak and reveled the moans that escaped her lips. “Oooh...y-your hands are so rough.”

Her half-hearted pleas fell on deaf ears. Gray’s decorum and manners were pretty much lost in the heavy steam of the sauna. His aching feet and arms had gone numb, leaving only the delightful sensations in his hands and around his dick. It felt too good...and he just let go.

“Aah?!”

Johanna froze in shock as rope after rope of syrupy spunk impacted her womb. Her velvet walls gleefully sucked it all up as she felt every moment of it. Her hips tried to wring out some kind of orgasmic pleasure to match, but simply couldn’t reach the lofty peak she needed.

Their combined gasps rang out for a few minutes before dwindling to silence. Gray went limp beneath her as he fought to stay conscious. Between his sudden exhaustion and the ever-present heat, this was proving to be a challenge.

She waited until he finished and went limp before trying to extract him from her pussy. A few errant ropes dripped out before her lips sealed back up again and hit the tiles below the bench.

“Are you usually this fast, or this...thick?”

She reached over and stroked his soft cock, sullying her hand in cum. Gray tried to explain himself. “I-I usually last longer. My apologies, Ms. Johanna.”

“I’m sure… still, that’s quite the load off, isn’t it?” She waved off his concerns, content to simply play with the load between her fingers. On a whim she brought her ring finger to her lips and popped it right in. the other digit quickly joined in as she suckled the salty treat. “ _ Pwah!  _ Mmm, it's quite good too.”

He watched the bead of spit drooping out of her lips before it was scooped up by her roaming tongue. He struggled up until he was sitting beside her. “T-Thank you for your service.”

Johanna giggled at his labored role-reversal of words. “I wouldn’t be much of a coordinator if I missed such obvious details.” She reached down and gently brushed his cheek, offering him a comforting smile. “Tell you what - let's go back to my room and grab lunch. Then you can take over the rest, okay?”

* * *

Gray tipped back the rest of his supplement pouch before tossing it in the nearby sink. He still wasn’t sure what all was  _ in _ those things, but they did their job well enough. His lunch break was almost over, and he’d have to make it to a reserve room to pick up a new suit.

_ “Mmmph, mmph, m-mmmm~” _

He glanced down at Johanna, happily on her knees and sucking him off. She’d already taken him down her tight throat and was gleefully choking herself on his prick. Her breasts bounced free from above her pulled down shirt, while her tiny black side-tie panites did nothing to stop the dripping on her kitchen floor. A pair of fuzzy slippers were all that kept her toes from the unforgiving chill.

“Mmm,  _ osh shoo gauud~” _

Gray groped the counter as her garbled praise sent shockwaves through his loins. The vibrations of her adorations wracked his still-recovering body as the supplements kicked in. He barely even felt her pull up to start flicking the crown again before it was over. “J-Johanna!”

His warning came too late, and soon her mouth was flooded by his latest offering. Her eyes widened as the MILF struggles to swallow as much spunk as she could. Her throat bulged out as she loudly gulped down full mouthfuls of cum, with a few big streams dribbling down her chin.

Finally, it dwindled away again, and she was safe to finish without drowning in seed. She popped him out of her lips, smacking around the taste of rich, tasty cum. “Sorry about that - got carried...away…”

Her fingers squeezed his cock, expecting it to be limp again. But she found a solid, potent rod ready for more raming. Johanna gawked at the marvel before her before stuttering out, “Y-You’re still hard?”

Gray helped her up, not even wincing at the squelching noise between her fingers. He waited till she was on her feet before wiping off his hand. Johanna meanwhile was reaching for a glass of water as he tried to depart. “Indeed. I want to thank you for your hospitality, but I must be getting back to-”

_ ‘Beep beep!’ _

_ ‘Beep!’ _

He blinked at the trio of beeps. The first two were clearly from his Xtransciver telling him his lunch break was up, but the other one...that came from Johanna’s Xtransciver as she swiftly reserved him with one hand. The Sinnoh MILF dropped her cup in the sink and tossed away her device before approaching him with a predatory smirk. “Leaving so soon?”

He returned her smile in kind. “Apparently not.”

That was all she allowed him to say before leaping on him in a feverous kiss. Her newly washed mouth felt cold and left a trail of goosebumps down his back as he fought her tongue for dominance. Their hands roamed each other’s bodies freely, with him grabbing her breast again, and her diving beneath his unbuttoned dress shirt. His hard cock prodded against her panties, mixing cum with quim.

They grappled, trying to claim the others precious mouth. Their feet danced awkwardly around the kitchen until her back landed against the fridge. Johanna’s eyes flew wide as she screeched, “C-C-COOOOOLD!”

Gray pulled back in shock, taking her with him. He held her close in his arms and let her feel his warm skin. His palms gently stroked her frigid back. She weakly mumbled in his chest, “S-Sorry...it was just-”

He shushed her with a single finger, causing her to blush like a mere lass. She let him guide her to a nearby wall dividing the kitchen from the sitting area. She arched back and sighed in relief at the much cooler smooth facade.

“Oooh, that’s better. Thank y-eeeeee?!”

Johanna squeaked as he rubbed against her panties. She blindly groped down for the ties and let the now-irksome piece of underwear detach from her hip. Gray wasted no time and sawed his way against her crotch until he finally managed to pierce her folds. “A-Ahh! W-What’s  _ in _ those things??”

“Everything I need to take care of my guests,” he smoothly explained. She wasn’t really interested in more quips and sighed in uncharacteristic irritation.

“Then stop stalling and start  _ fucking _ .”

“As you wish.”

_ PAP PAP PAP PAP PAP _

Johanna’s nails dug into the fascia of the wall as she struggled to hold on. Her toes were screaming from how long she’d been on her tips as her thigh squeezed against his back. She swore she heard the beep, but that was only a few minutes ago...or maybe it was ten?

Gray was in a slightly better state, thanks to his lunch’s boost in energy. He glanced down at his Xtransciver between thrusts and confirmed there was still a good bit of time left. Just enough to utterly creampie this MILF before he had to dash down the hall to grab a new suit. But before then, he wanted to give her something that she’d long since been due - an honest to Arceus orgasm.

Her moans morphed into wordless screams as he sped up. He abandoned her hips in favor of pinning her between the wall. Her own hands flew up and dug into his shoulders as he knocked her clear over the edge. “OOOOOOH~”

He struggled to thrust in her now-unbearably tight pussy. The hot juices basting against his dick were all he needed to know he’d done his task and could finish things properly “J-johanna, i’m so close. Where do yo-”

“INSIDE! CUM INSIDE ME-EEEEEEEEEEEEEEEEYAH!”

Shrill screams echoed off the soundproof walls. Her nails scratched against his back as he pumped yet another load deep in her waiting loins. It mixed and sloshed with his earlier cum, setting off maternal emotions that had been buried for far, far too long.

He was atop her before she even noticed, already invading her gaping mouth with his tricky tongue. The MILF tried to put up a token resistance but couldn’t even hope to match in her current state. She let him ravage her mouth as he pumped more and more cum in her needy womb.

Johanna pulled back, gasping for breath in the face of Gray’s barely winded grin. Somehow she found his calm smile less mocking and simply...relaxing. “Y-You know, if you’re ever in the Sinnoh region...muh, my daughter has a villa she barely uses, and I have a key... if you’re interested~”


	5. Lola

**Notes for the Chapter:**

> Not sure if anyone was really looking for more of her, but here she is regardless! fair warning - I can't quite recall her that well so she might very well be OOC. Still, enjoy :)

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

It was almost after hours, and everyone was once again out on the beach to celebrate. Gray arrived at the solarium to clean, decked in a fitting pair of shorts and a shirt with the hotel’s logo on the lapel. As soon as he stepped onto the deck, he immediately saw that one of the jacuzzis was still occupied. Yet another delectable MILF - Lola of Kanto.

From what Delia had told him, their sons had often traveled together. The two mothers weren’t exactly close, but they were familiar enough together now. Speaking of being a mother, she certainly didn’t look like the type that had already had almost a dozen children.

He stared at her, slightly lulled over in a peaceful slumber. The waters were warm and bubbling, but not quite enough to be a threat to her safety. Instead he could admire her looks freely. The way the ambient lights of the hotel and the moon graced her body. A full feminine figure, wavy brunette hair, and a slight tan thanks to the Alolan sun. 

Gray was hesitant on what to do - his current responsibility was to the pool, but she was also a client of his. Ultimately he settled for reaching down to gently nudge her awake. “Excuse me, madam? The pool will be closing soon.”

“Mmm...w-wha?”

Lola stirred at his touch, shaking off the lethargy. He noticed her attire was a simple one piece bathing suit, albeit one that was straining against her curvaceous, full figure.

She rubbed her eyes clear before finally seeing his presence. “Oh hello! I didn’t expect to see anyone out here...my word, it's gotten dark out!”

She shifted up, letting her bosom clear the bubbly surface. A deep stretch pushed her back up and made her tits almost pop out of her swimsuit. “ _ Ahhh... _ Are you here to clean? Wait, is it really that time already?”

Gray confirmed her suspicions with a disarming smile. “I’m afraid so Ms. Lola. You also missed dinner, by the by.”

Lola chuckled at the side comment. “Heh, I guess I dozed off...didn’t realize how late it was.” 

“I’m sure. Shall I help you to your suite? I could also contact the kitchens to bring you something.”

The MILF shook her head but tried to appeal for more time. “Surely you could give a poor ol’ mother another thirty mintues...couldn’t you?”

He was ready to rebuff her for proefssionalism’s sake. Lola’s little lip bite made it quite difficult. Before he could shut her down though, her eyes lit up as a devious smirk graced her lips. She flicked open her Xtransciver...

_ Beep! _

_ Beep! _

“Or...would you like to join me,  _ Nidorino _ ?”

* * *

_ ‘Mmm~’ _

Lola’s head tilted back as she let the young man take over their kiss. Her body felt numb from hours in the jacuzzi, and there was a constant little battle to stay alert in the lulling warm waters. He was already under her swimsuit and groping her tits. Just like she wanted.

Tonight she was simply enjoying herself - no longer having to worry about her kids or husband. The couple had already talked about this trip, as well as the extra ‘packages’ it would offer...needless to say, she was quite interested to get started.

She pulled away, leaving a trail of spit between them. Her tired legs carried her to the nearby wall. The water came up to her thighs, barely leaving her succulent swaying hips above the surface. Lola reached down and pushed the bottom of her swimsuit aside to expose her gushing pussy. “Right here - do me now.”

Her order flew in the face of all the health and sanitization standards of the Hotel, and the island as a whole. But she was also a guest of the all-expenses paid and exclusive Nidoqueen Package.

Of course he obeyed.

“Ooooh...s-so thick~”

Lola’s coo sent a twitch of pride through his body, right down to his dick. He pushed up until she was stuffed full of his bone. “Ah!”

Gray’s hands seized her shapely hips as he basked in her lavish praise. His bravado ultimately got the best of him. “Is that deep enough for you, Ms. Lola?”

Lola tsked at his misplaced pride. She turned back to face him, a wink peeking out between her curly locks. “Who can say? But I think you’re wasting my time with the chatter. Chop chop, Nidorino - lets see some  _ Hydro pumps~ _ ”

He complied with her request and swiftly started ramming. Their hips sent splashes of bubbling water over the edge and into the adjacent pool. Rippling flesh sent rivets of water and sweat off their writhing bodies.

The MILF panted, feeling the delightful heat in her churning pussy. Feeling a nice, hard cock in her slipper twat in a hotel’s public jacuzzi at night - she’d hit the jackpot, big time.  _ ‘Oooh, Clint - this is the best anniversary gift you could get me, and all I had to do was let you keep the musty old rock gym?’ _

_ ‘I owe you big time, darling~’ _

Gray reached down from her shapely hip to her dripping pussy. He leaned in and suckled her delectible neck, getting a nice whiff of her perfume in her bouncy hair. His fingers traced around her slick swimsuit and partially-exposed muff until he found his prize - her little pink nub.

“HEEEEEEEEEEEEE-!”

Her shrill voice broke the rest of the placid silence. Gray acted quickly and brought his slick digits up to stuff her open mouth. She had the fortitude to not bite down and simply started suclking his tips. His fingers pumped in and out of her mouth. Her tongue danced between his slick digits, tasting her own juices.  _ ‘I taste...good.’ _

He kept thrusting, enjoying the cool slippery tongue dancing between his fingers. His other hand came up from her hip to her breast and started rolling and tweaking it from inside her tight swimsuit. It was too much for her.

“I’m...Iiiiiiiiiiii’m!”

Lola buckld forward as an orgasm tore through her body. Her head dipped down into the pool and ruined her curls.her numb legs started floating in the shallow jacuzzi around his sides.

Gray pulled her back up to the jacuzzi before finally pulling out. He eyed the telltale wads floating in the bubbling water. The jacuzzi would need to be purified overnight for the other guests. But as with every other health violation, Lusamine insisted that the ‘cleanup’ crew would handle it.

_ Brmmm... _

Lola shook off her climactic stupor at the sound of thunder. “Oh...it’s going to rain.”

“So it seems.” 

The MILF turned back to him with an inviting smile and spark of lust in her winking eye. “Why don’t you finish cleaning up and join me upstairs for dinner...in my room?”

* * *

Gray stretched out in the chair, relishing the cool wind and occasional spray. His eyes had already adjusted to the dark and could make out the absolutely sexy sight of a MILF straddling his bare lap.

After hours meant Gray could do whatever he wished. Usually it wound up being nothing since he only had precious few hours to sleep before his next full-day shift. But if he wanted he could go anywhere in the hotel, or even bring one of the lovely ladies of the Nidoqueen Package back to his room for some prolonged action. He didn’t even need to  _ stay _ in his own suite for the night in fact.

Such as now.

Lola’s plump ass rolled over his erect cock. Her feet clung to the sides, relying on the support of the armrest to keep her atop him. She’d traded her rumpled swimsuit for a saucy looking sheer camisole, already wet from the rain blowing onto the balcony. All lights were off now, except the few that peeked out from within her suite. The couple were cast in utter darkness, alone and overlooking the crashing waves of the Alolan seas.

Gray shifted until his cock had traced beneath her legs and settled between her holes. “How do you want it, Ms. Lola?”

The MILF growled, lost in the heavy rain. “I want it dirty - the dirtiest you can give me.”

Her insistence sparked a fire in both of their loins. Lola rolled her hips so that his head was pointed right at her puckered rear. An earlier bout of devout cock worship had ensured his dick was slick and ready for her. “Now shut up and fuck my ass.”

She pushed down, but only enough to have him poke through her asshole. Lola hissed, bunching her fists up until her nails left marks. Her toes curled against the iron lining of the chair as she struggled to adjust.

Anal wasn’t new to her, but it wasn’t something she’d partaken in regularly. It took time and patience, but eventually she managed to fully sit on Gray’s lap with his thick cock stretching out her butt. Sitting turned into tepid strokes, storkes morphed into bouncing, and bouncing eventually turned into what they bot really wanted - hard, fast fucking.

The chair squeaked beneath them as their hips smashed together. Lola’s fat ass rippled with every impact and sent delightful waves across her fair skin. Her feet had found ground at the chair’s side and now kept her firmly in place, allowing her thighs and glutes to pull and push against his erect pole. The MILF’s lustful coos only grew as she reached up and began tweaking her sheer-covered breasts.

Gray was honestly content as things were. He didn’t even need to know how long they were going. Being off the clock meant he didn’t have to worry about how long he’d been fucking for, or having to finish up at a reasonable pace. Sure he may not be getting paid in pokedollars, but an ass like this?

Priceless.

“Fuck...s-sooo good.”

Lola’s praise stirred something in him, but he was more cautious about how he expressed it this time. “Good enough, Ms. Lola?”

The MILF shook her bouchy brunette head. “Fuck no!- t-take me to the railing.”

The two shimmied forward until her feet were off the edge and touching the ground. Without ceasing, they slowly rose as one until she was able to grip the balcony railing for support. Gray’s hands shifted from her hips up to her breasts, feeling how cold they were in the rainy night air.

She leaned over the railing and let her camisole grow damp until rock-hard nipples stuck out. Her nails scratched against wrought iron bars. She couldn’t help but hiss and blurt out, “Ohhhh Arceus...it feels so good, Gray~”

The moans and mewls from her lips carried another message, another meaning. In truth she felt a little guilty- the mood would be perfect for romance and passion, but was squandered on mindless, wanton rutting. Even saying his name felt...off, at least compared to the little pet name that she had to use to ‘book’ him.  _ ‘When I get back Clint...you, me - the first stormy night at Pewter Gym.” _

Her wistful thoughts were shattered as she felt Gray bottom out in her bottom. Hot spunk flooded her ass and made a nice, sticky mess of her rump. Adulterous screams were lost in the pouring rain.

Gray pulled her back into the chair, holding her as she rode out sensuous seizures. His own mind was a bit hazy, but he could focus on one thing at least - the rain.

Rain always made him wistful and nostalgic. Back to the days in Po Town with the gang. Never once did he imagine he’d be here in life. Working with a classy ass hotel, being paid top dollar to fill space and be a walking dick for a bunch of horny MILFS. He didn’t know who to thank between Arceus and every other ‘mon in the Pokedex...but here he was.

He’d catch hell tomorrow. Tonight was heaven...


	6. Keneko

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

“Good evening, Ms. Keneko - I’ve brought you your drink.”

The MILF tilted up her glasses and blinked in the low afternoon light. The sunset cast a rich amber over her plain sundress and accentuated her developing tan. Her eyes lit up as she marveled the nice, tall glass on a platter just in front of her. She brought up her lounger’s back so she could enjoy it properly. “Oh, Alola, sir! Thank you!”

Gray withdrew the platter and kept it at his side. His smile was as professional as he could make it, even if he felt a niggle of contempt towards the woman in front of him...or rather, _who_ she was connected to.

From what he understood, this was the mom of the kid that broke up the gang. A part of him still felt spiteful at how that happened, but then another part could be rational about it. The ridiculous amount of money he was getting a day certainly helped. So he elected to stay composed and attentive, treating her the same way he treated the rest of their ‘guests’.

Keneko savored the sweet taste of her fruity drink. “Ahhhh, that hits the spot. Can’t get anything like this on Melemele, not even in Hau’oli City!”

“Ah, is that where you’re from?”

His words were already out before he could bite his tongue. A silent curse passed by her inquisitive face before he tried to save his butt. “Must’ve been a nice, short trip over here to the hotel then.”

“Yep! The house is nice, close to the beach and everything. But it doesn’t even come close to _this_.”

He sighed, glad she seemed to have taken the bait. Despite his misgivings, he didn’t exactly feel any malice towards the MILF - sure she was a bit too enthusiastic, but it was also rather charming to have her smile greet him in the halls or on the beach.

Keneko nudged him out of his musing. He stared down at her wistful smile. “You know what the best part is though. Here I’m not just a stay-at-home mom, sitting at home with her Meowth. Here I’m treated like royalty...pretty nice, huh?”

HerShe brought a hand to her chin and mused aloud, “Perhaps tonight… oooh.””

Gray felt a shudder run down his back, and almost regretted asking what she was planning. “Ms. Keneko?”

His question made her laugh - a high-pitched, almost fake-sounding guffaw. “Ha ha ha! Oh ignore me - i’m just a lonely woman at night, hoping nothing _unsavory_ happens to me.”

Keneko rose from her lounger with a beaming smile. She brushed the wrinkles out of her dress before dropping her glasses back down over her eyes. “Well I’m going to check out the pier - good evening, sir~”

Gray watched her walk away with a spring in her step.

“Ms. Keneko, you forgot your...hat?”

He noticed something else under the brim - some fresh towels from her stateroom. Not really the kind that were suited for the beach. He counted one hand cloth and two towel sheets more suited for covering hair. “Why did she leav-”

_Beep beep_

The subtle beep made him jump. He should’ve been used to the telltale call now, but there was something about this particular circumstance that left him a bit on edge. Gray glanced down and bit back a groan. _‘really?’_

He’d been reserved - by Keneko. Things were starting to come together as he gathered up her discarded effects. He hid the towels in her hat before looking back to his Xtransciver. Gray tabbed over to the comments, already guessing what he’d see.

**_'Roleplay - towels and a mask ^3^ <3' _ **

He Looked down at the towels and sighed.

_‘This feels like typecasting.’_

* * *

Keneko’s screams were muted by the towel stuffed in her mouth. Her wrists struggled against the coarse wrap binding her arms in front of her. She couldn’t see anything but little slits of light through the weaves of her hat, now shoved over her head. All she knew was that she’d been bent over a mooring post and was now being savagely fucked from behind. Shock and fear had gripped her heart...and she _loved_ it.

Gray’s gritted teeth were hidden by the handcloth. A pair of small fish hooks and wire had made it into an impromptu mask, partially concealing his identity. It kept his hands free to wrap around her waist or snake under her armpit to fondle her tits.

Knots came easy to him - lots of that kind of stuff back in the gang. Then again, knowing a bit about sailing and knotwork just came naturally to an Alolan naitive anyway. He’d played his part of the session well, using years of experience in the gang to ambush her and steal her away to the far end of the pier. If anyone were to stumble upon them, it’d look for all the world like outright assault.

It was anything but.

Keneko was in utter bliss as she lived out her deepest, most twisted fantasy. The Unovan MILF liked it _rough_ \- and this little vacation her daughter had set her up on had been the perfect excuse to indulge in that fantasy. _‘Oh honey....if you could see your slutty mama now.’_

Gray pushed her against the post and kept her pinned by his gyrating hips. His arm slithered out and around to grope her jiggling ass. Her yelp of shock barely made it past the spit-stained cloth between her teeth. She’d given up on pretending to be a victim and was now actively undulating back against his hips.

_Pap pap pap pap pap_

“ _MMMMMPH!”_

“Champ?”

Gray acted on instinct and quickly pulled Keneko back out of sight. His hand had escaped her tits in favor of clamping down on her mouth. He didn’t dare move, dare speak, even breath was too risky in the looming shadow of the mighty Machamp.

The MILF thrashed in his arms, eager to milk his trapped cock. She didn’t see the danger, or even hear it. All she knew was that he’d taken her somewhere, and the sensation of not knowing was making her already twisted fantasy practically peak. Her gushing walls squeezed tight like a vice...and finally coaxed him over the edge.

_‘S-Shit!’_

He bit his tounge to keep from roaring out and alerting the suspicious Pokemon. His loins were far less composed and were in the process of filling her neglected womb to the brim. Gray felt the adreniline and the fear simply...evaporate. Melt awy as he leaned into the explosive orgasm. _‘Fuck it...if this is it, it ain’t so bad.’_

“Mach…”

The Machamp shook its head and proceeded back up to the hotel grounds, leaving the duo to convulse in darkness. They slid down against the hard pier planks, gasping and wheezing for breath. He smacked his wrist to keep the timeout alarm from ruining the moment. Eventually he gently removed her hat and set it on the nearby ledge.

Her vision returned to the sight of the early evening. The sun had set some time ago, casting the island in the cool light of the moon. She felt the knot loosen around her nape, letting her spit out the gag and drop it over the edge of the pier.

Gray unbound her arms and used the towel to clean her loins, wiping away as many juices and stains as he could muster. Decorum was fueled by adrenaline as he struggled to dispose of the metaphorical evidence. The cleaning crew was already impatient with him, and the last thing he wanted was to evoke their wrath.

Keneko offered only meager aid as he struggled to adjust her back to decency. Her panties shifted back around her stuffed pussy, and her dress smoothed over her damp thighs. A cursory glance would suggest that she’d merely finished running...in a sundress.

At night.

“M-My room - one hour.”

* * *

_Thud!_

Keneko’s head smacked against the glass door. Her vision blurred for a moment, but the relentless barrage of pleasure kept her focused on what mattered. Her wet, matted hair clung to her glistening skin as she matched Gray’s thrusts, suspended only by his palms digging into her fat ass..

The low sunlight turned her room gold and cast brilliant light upon the copulating lovers. Her robe hung from her wrists, her legs locked against his firm back. His dick was back where it belonged, sawing in and out of her sopping wet pussy and making it filthy after her brief shower.

Gray leaned in and attacked her neck, leaving a flurry of licks, scrapes, and nicks behind. He wasn’t letting up, not after her last session caused him so much stress He’d made sure to take a supplement along and chugged it before sneaking into her room, like she’d wanted.

Keneko’s eyes rolled back as her body lit up. Her back pressed against the balcony door with her bare ass rubbing against the cloth. Sweat and water poured down her body, making her shower utterly pointless.

He pulled away from her neck in favor of her shoulder. Gray adjusted the MILF in his arms so he could comfortably nip her collar before lavishing kisses near her armpit. He noticed tiny, trimmed tufts of hair under her arms. _‘Never took her for the type.’_

Keneko’s flushed face darkened as she felt him near her armpits. “D-Don’t do that - it’s fith-eeeeeeee?!”

Gray’s tongue licked her pit clean of shower and sweat. “Seems fairly clean to me,” he quipped before adjusting her again. Her loins clamped down on his dick as he brought his attention to her perky breasts. “I can take care of these, too.”

“OOOOH!”

Her screams deafened him, but he spurred on and started lavishing her tits with the love they so dearly needed. Her thighs squeezed him tighter and closer, limiting how far he could thrust out and putting him at the edge of his limits.

Gray doubled his pace until the slaps were almost deafening in their ears. He pulled away from her rock hard nipple leaving only a trail of spit behind. His dry throat scratched out, “Where d-damn!...-ou want it?”

She struggled to speak through her heavy pants. Drool and slobber gave her eventual words a heavy slur as she screamed, “O-Ohn mye faaaaashh!”

Gray was confused, but obeyed. Her legs fell limp and released his back, finally allowing him to pull out. Keneko slunk down until she was on her knees with his dick smacking her forehead. Her tongue snaked out and lashed against his sweaty sack. “K-Keneko!”

The MILF shrieked in delight as she relished her second shower. Hot spunk clung to her face, mixing into her hair and forcing her eyes shut. She kept her mouth open for any errant shots to land on her waiting tongue.

Gray fell back into the nearby chair, gasping for breath. His heart was still racing from the MILF’s twisted games, especially the stunt on the pier. _‘S-She’s freaking nuts.’_

Keneko wiped her face off with her robe’s sleeve, letting her finally open her eyes. Crusty cum cracked as her eyelids rose, revealing the shining, mischievous gleam within. “Oooh...W-What do you say to a trip into town tomorrow? I saw a nice alley when I came here~”


	7. Caroline

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

The northern most beach was usually abandoned due to its long trek from the hotel grounds. Still, there were often guests that simply wanted to bask in the Alolan sun without the hassle of or convenience of the hotel’s luxuries. Such as the Hoenn beauty currently lying in a lone lounger on her back - Caroline.

Her connections into the Nidoqueen Package were fairly standard. Wife of a celebrated gym leader, mother of a regional champion - nothing too outstanding beyond those. What _was_ exceptional about her was her hot, tight body and unbelievable beauty. The short bikini barely covered her body, ensuring optimal tanlines.

Gray wiped his brow from the heat welling around him. His shorts were going to make it awkward if he wound up getting ‘up’ all the way out here. Instead, he kept his ogling to a minimum and handed her a new bottle of sunblock.“Good day, Ms. Caroline - Here’s your sunscreen, as you requested

The MILF rolled over and tilted down a ritzy pair of sunglasses. Smoldering eyes blazed hotter than the sun as she drank in her personal beach boy. She was far less composed in her own appraisal before nodding in approval. “Fantastic - I didn't expect it to get quite so hot out here.”

“Indeed, perhaps you’d prefer to go back to the main area? There’s more shade there, and our accommodations are much closer for you..” Gray suggested.

Caroline hummed, as if pondering his proposal. Her palm reached down to graze against her bare, tanning thigh. She stared up at him with eyes and a smirk that just screamed trouble. “Mmm, isn’t that what you’re here for, my dear? Perhaps...I simply wanted you all to myself?”

Gray tried to keep his composure, especially knowing what his extra criteria for the Nidoqueen Package entailed. “I ah, well that is-”

Her sudden laughter cut him short. “Ah, hah hah hah hah hah!”

He watched Caroline laugh herself into fits, rolling between the arms of her chair. Her bouncing breasts were worth whatever humiliation he was enduring. Eventually she settled down and wiped away a tear in her eye. “Ah, sorry about that. Its very kind of you to come out all this way for me, though.”

Gray’s smile resumed as he put his professional face back on. “Oh course, Ms. Caroline. Is there anything else you require?”

The MILF returned his smile as she leaned back. “Oh yes- would you mind getting my back?”

He paused, fighting back the desire to jump her on the spot. Decorum and discipline won out...as well as the incentive of waiting for the right moment to earn double time. “...if you wish, Ms. Caroline.”

The MILF was already reclining back before unclipping her bikini top. “Oh trust me - I _do.”_

Gray lathered his hands up before placing them on her bare shoulders. Caroline cooed at the cold touch, but made no move to stop him. She let him lather up her shoulders and nape before moaning out, “Mmm...lower”

He gladly complied and started lubing up her hips. His fingers meshed into her sides, like her baby-borne hips were made for his clutches. _“Lowwerrr~”_

His palms slid down and around until they were cupping her supple rear. Globelous checks that bounced with every shake or squeeze.”Oooh...that’s it.”

Gray breached decorum and wound up straddling the chair, looming over the temptuous MILF. his weakened restraints struggled as he tried to keep playing things off. He kept her thighs pinned under him, giving her the slightest touch of his looming excitement. Caroline certainly didn’t mind. In fact…

_Beep! Beep!_

She turned back to him, letting her fingers drop from her Xtransciver. There was no mistaking what was burning in her eyes now, especially not with the drool dribbling down her chin. “I said I wanted it on my _back,_ Nidorino...but maybe it’d be better _in_ , wouldn’t it?”

* * *

_Creak creak creeeak_

The empty bottle of lotion lay forgotten in the sand. The chair’s groans were drowned out by the dulcet, erotic mewls and moans from the duo on the beach. Her thong was down by her ankles as her rump shook in the air.

Caroline’s nails dug into the lounger’s straps beneath her chin. Her body shook with every vigorous thrust. She felt her nipples painfully rubbing against the material of her bikini top. “Oooh...you know the pace I want, don’t you Nidorino?”

Gray grunted, “O-Of course Ms. Caroline.” He gripped the armrests for support and let his hips do the rest. The sunblock made the task of percing her butt just bearable enough. _‘F-Fuck - she’s so tight!’ “_ Is tha-shit!...is that to your liking, M-Ms. Caroline?”

The MILF actually growled, much to his shock. “Drop the ‘Ms.’ shit and keep going, kid...actually, speed up.”

He obeyed, letting his hips do the talking. Caroline grunted in approval as she adjusted to having her ass stuffed with cock. She wasn’t exactly a novice in such matters...but it’d been so long that the pain was chewing her body to pieces. She bit down on a chair strap to keep from outright screaming as she got what she finally wanted - a good pounding.

Things with Norman were...rocky, to say the least. He hadn’t even seen her off before she departed for Slateport and the cruise to Alola. She at least understood why her daughter was absent - being the regional champion cut into your free time after all. So she’d had a lot of time to think about what she was doing...and once she set foot in the Hano Grand, Caroline was convinced she’d made the right choice.

The MILF spat out her chair strap long enough to bark, “I said faster...and _harder!”_ Years of loneliness and pining were burned off as her ass was smashed against his hips. Her nails dug into her palms until there were little nicks of blood in her hands.

It wasn’t enough, not for what she needed. Caroline was done with being coy. She didn’t want a horn attack - she wanted a horn _drill_.

Gray reached down and seized her hips. His feet planted on the sand as he proceeded to _really_ hammer into her, like she wanted.

The mark on her ring had been tanned over nicely, thanks to hours up on the sundeck of the ship. She’d be keeping her band off for at least the duration of her stay here in Alola. One of th escant few to know her marital status was currtenly fucking her ass, and she’d perfer to keep it that way.

The two were lost in their own sinful world, nestled only by the rocky cliffs from the rest of the hotel’s beach. The crashing waves masked their moans, but occasionally a high pitched shriek would reach above the crests. They could be caught at any moment...neither one cared.

Gray’s hips were a blur as he pistoned in and out of the Hoenn woman’s ass. Their impromptu lube had nearly dried up due to the friction of rutting. A noticeable puddle had formed just beneath her gushing pussy, staining both the lounger’s straps and the sand beneath. Caroline had abandoned the strap in favor of simply biting her lips until they bled. Their undulations brought them both right up to the edge...and then over it.

“C-Caroline I’m gonna-!”

“OH F-FUUUUUCK!”

The MILF collapsed onto the shaky lounger as thick, gooey spurts of hot spunk filled her ass. Her engorged clit wound up pinched between two straps, keeping her in a constant state of euphoria as she took every sticky rope. Her world was white now - a featureless mass of pure light that consumed every sense of her being.

Eventually, the world dimmed, revealing the bright Alolan noon. Gray shook away the stars and gulped down heavy doses of salty air. To his shock, he realized he was still cumming, albeit at a much slower pace. _‘Arceus above...what a woman.’_

Caroline whined as he pulled out of her butt. A last spurt of jzz smacked against her cheeks. She finally turned back and showed her nicked lip and dried tears. “Y-You really stuffed me full...I don’t know if I’ll be able to walk for a bit.”

_Beep!_

Gray winced as their Xtranscivers signaled the end of their session. The soft chime was almost pounding in his post-coital ears. “Will you ...be okay here, ma’am?”

Caroline waved him off, not even bothering to attend to her messy bottoms. Instead she simply spread her legs, the laborious act rewarding him with the sight of his cum bubbling out of her packed ass.“Come back by my room later - I’ll be waiting~”

* * *

“F-Fuck! Your throat is tight…”

Caroline’s response was a wet gurgle as her cheeks billowed in and out with every vigorous thrust. Her bare ass rubbed against the cold countertop as she endured his through cleaning of her tonsils. Tanned, supple legs drooped over the opposite edge and knocked against the sides.

“F-Fuck! I’m cumming!”

The MILF’s eyes widened as her nose was stuffed against his crotch. Thick, viscious spunk filled her throat and threatened to drown her in jizz. Caroline’s fingers dug into the edge as she struggled to swallow it all down.

_“Ulp, ulp, ulp…’_

Gray pulled out and aimed his dick at her bare, drooping tits. Sticky spunk slapped against her breasts, painting them in white. Her head drooped down as she gargled and coughed cum. His loads dwindled away until he could only offer a little spurt into her disheveled hair. “Damn, C-Caroline that was…”

The Hoenn beauty struggled to roll over, smearing her counter with cum. She tilted her head back and swallowed the wad in her mouth. She wiped away the rest before hoarsely declaring, “Oh trust me - this is far from over.”

His weary body was suddenly alert - he wasn’t really sure how much longer he was gonna last, especially with the reserve time coming so quickly to an end. Lusamine had told him that as much as he was there to be ever horny mama’s cock to ride on, he had to firmly establish and lay down the boundaries.

_“It wouldn’t do for you to be too exhausted or unavailable for hours on end.”_

“M...Ms. Caroline, while I would like to oblige your request, I regret to inform you that your time has ex-”

_Bzzzzzt_

Caroline reached out and playfully flicked his cock. Her other hand was perched in her cheek, looking rather coy despite her state of undress and coated in sin. “That’s your clock out, yes? Meaning you’re free for the rest of the evening?”

She didn’t even give time to answer before she pulled him back to her by his dick. Her tongue lashed up his girth, leaving a long trail of spit from base to tip. “Well then...let’s just say you won’t be leaving until tomorrow~”

* * *

Gray tried to pull his uniform back together. The time was blaring at him. The room was still dark, as expected. Still, the pale moonlight cast a sensuous trail of light over the messy room and its satisfied, stirring MILF.

Caroline watched him with lethargic amusement. Her nail reached down and tapped her sore thigh. “You know, if you come back over later...I have a shirt I think you’d be interested in seeing~”


	8. Kuroru

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

She brought her glass to her lips and tasted the finest wine in all of Alola. “Ahhh...This is so nice - I don’t usually get to dine out like this anymore.”

Kuroru from Unova. Standard faire of a son who was his region's champion...or rather, ‘former’ champion. Apparently he’d up and left one day following some other kid around the world. Still, his mother wasn’t all that worried, especially not when he’d gotten her a full expense paid ticket for the Nidoqueen Package. Now she was here - enjoying a ritzy private dinner with a simple yet lovely black dress and stockings.

Gray was acting as her ‘date’, at a special request from the boss herself. A nice, matching parlor jacket over his usual attire had done the trick. He certainly didn’t mind an hour off his feet, enjoying an actual meal with a gorgeous MILF like her. “Not many places like this near you?”

She chuckled. “Well that’s true too. But when I was a trainer it was like this all the time. Nice fancy restaurants, good accommodations, you name it.”

He raised an eyebrow at her boasting, deciding to humor her and get a little more than what her dossier had entailed. He leaned in, letting his voice reach over the smooth music around them. “Oh really?”

Kuroru nodded as she buttered up a slice of bread - the kind that was worth more than a ticket to Castelia City. “What can I say - I was a force to be reckoned with. I tore through Unova like a wildfire.”

Gray whistled in admiration. He cut off his own piece of bread before commenting, “Didn’t expect to meet such a renowned trainer...how far did you make it?”

The MILF waved him off as she sipped more wine to wash down her appetizer. “Oh not that far - earned a few badges but never really got into the whole ‘training’ aspect.”

“Then how did you afford all those nice places?”

He could already guess, even before seeing her coy face hidden behind her half-empty glass“Well...there are other ways to pay for services after all.”

“...I see.”

Kuroru frowned, taking his simple reply as disapproval. “Oh don’t be like that - especially not when we both know what this was about... _ Nidorino _ .”

Gray raised a brow before popping another slice of bread in his mouth. He watched her go through the paces to reserve his time (more so than she already had) before turning back to him. The MILF gestured behind them to the rest of the long, thin private room. “Keep an eye out for the waiter- i’m feeling peckish~”

* * *

“Are you ready to...Oh.”

Gray relaxed his clenched face before their waiter came into view. He felt Kuroru’s lips slow down and hold his dick near the back of her mouth. Her tongue slid up and down his shaft at a lazy, languid pace.

“..Evening Dustin - I believe we both are ready.”

The waiter crossed his arms, letting the meticulous charade drop. “Really...so where’s your ‘date’. Gray?”

Gray leaned in, trying to keep the MILF’s head completely out of sight. “She stepped out for a moment,” he explained. Said ‘date’ resisted the urge to loudly slurp, not trusting the ambient music to cover for her cheeky antics.

Dustin wasn’t buying it, but not for the reason that Gray was trying to hide. “I see...Shall we wait for her to come back before ordering?”

In the darkness, Kuroru rolled her eyes. She could already tell who this annoying waiter was - the same one that was ogling her as she was led to her seat. More than that, she knew his type - the kind of high rollers that she would tend to avoid unless she really,  _ really _ wanted a nice payoff for the disappointment. The MILF wasn’t willing to deal with this farce any longer, and prodded Gray’s thigh with her manicured nail.  _ ‘Wrap it up!’ _

He covered his wince with a brush of his eye. “That won’t be necessary - I have her order right here.”

“And what will  _ she _ be having?”

_ ‘Ugh…’ _

She started bobbing her head, going slow enough to keep things down but fast enough to be noticeable .Kuroru wanted the waiter gone so she could enjoy her appetizer in peace. But as Gray prattled off on every meticulous detail of her meal she found herself growing more and more impatient.

_ “Urk!” _

Dustin glanced up from the list on his pad. “What?”

Gray coughed, trying to hide his outburst. “Sorry - something in my throat.”

_ ‘You mean my throat, kid.’  _

She waited till they were talking before quickly flicking open her Xtransciver.

_ Brrt. _

“Excuse me,” Gray paused and glanced at his screen. Under the timer was a new message - from Kuroru.

**_‘Knock three times and cough when he’s gone ...and HURRY.’_ **

“...And an extra side of butter.”

Dustin took the menus and stepped back. “Very well. Shall I bring it out with a cover for you... _ sir?” _

Gray shook his head. “That won’t be necessary - thank you, Dustin.”

He felt her slow down, barely even letting her tongue flick against his shaft. He resisted the urge to signal her until the door slid shut. She was completely still now - waiting for him.

_ Knock. Knock. Knock. _

_ ‘Ahe-eeem?!’ _

Kuroru’s lips slapped against his groin as she took him all the way down her tight throat. Her hair knocked against the table’s bottom, but neither one paid it any mind. They’d been left alone in the dining hall, and she intended to take advantage.

The MILF was  _ done _ with playing coy - she finally wanted to do what she;d been hoping for ever since she set up this date, and that was to fuck her throat until she was a sloppy mess. No more being quiet or composed - time to be a slutty mommy.

Gray’s fists bunched against the cloth, pulling up just enough to expose her legs. Kuroru ignored the sudden light and busied herself with noisily slapping her face against his crotch. Her gullet was stuffed by nice, thick dick as she pounded him way past the point of no return.

“M..M...K-Kuroru!”

The MILF squeaked in glee as she finally got what she wanted - a nice, hearty helping of butter to go with all the bread she’d had. Her throat bulged as she expertly swallowed every fist-sized wad.  _ “Sh-Shtill gaht it~” _

Her date collapsed back into his seat. He blindly passed down a napkin, which she gratefully took. Still bobbing against him, Kuroru busied herself with wiping her chin and cheeks clean. Her knees were getting sore, urging her back up from the table. She remembered what would eventually be waiting for her...and got a devious idea.

_ Brrrt. _

Gray tiredly glanced down at his Xtransciver at the new message.

**_‘Get down here - I’m gonna have a word with him >:)‘_ **

He returned the virtual grin with a smirk of his own. _ ‘This should be fun…’ _

* * *

So still waiting for your daaa...Ah, g-good evening, ma’am.”

Kuroru glanced up from Xtransciver, collapsing the side screen. Her fingers curled together as she cooly greeted him. “Good evening, sir…”

Dustin flinched, unable to meet her cool gaze. Instead he gestured to the two plates in his hands. “I ah...your dinner is here.”

She offered him a smile -one lacking in any warmth or goodwill. “Splendid - I was getting quite hungry.”

Between her legs, Gray had the decency to feel sheepish. He’d misunderstood her earlier tell and made sure the meal took as long as possible, thinking she wanted time to indulge. His apology came in the form of a slow, sensuous lick up her trembling lips.

“So where did G...your date go?”

_ ‘Not far.’ _ She hid the ghost of her smirk in her palm as she brushed her hair aside. “He was waiting for me to get back before excusing himself, like a proper gentleman. I must say, I’m...quite happy with the service your hotel provides m-me.”

“Wonderful. Here at the Hano Grand, we strive to offer our honored gu-”

_ ‘Ahem!’ _

Kuroru cut his canned speil off, directing his attention back to her less than hospitable visage. “I think that will be all,  _ sir.” _

“V-Very well - please enjoy, ma’am.”

“Oh I’m sure we will. Until then I’d like to enjoy my meal and company without...intrusion.”

Gray kept dutifully eating her out, even as he heard the MILF shut that insufferable git down.  _ ‘Hmph...we used to rough up pricks like that...gotta say, this is much better.’ _ he admitted as he let his tongue pierce her folds.

Kuroru’s sneer stayed in place even as she fought the urge to buck her hips down. She couldn’t even spare a glance down at the scrumptious meal before her. Her hunger went beyond a few quivers in her stomach - far beyond.

She didn’t want his tongue- she wanted  _ dick _ .

_ Brrt! _

Gray paused as he suckled her puffy lips. He glanced down at his glowing screen and the message within.

**_‘We’re leaving’_ **

He didn’t even bother with the charade as he pulled out and simply asked, “Not staying for dinner?”

“Fuck that. My room - now.”

* * *

Kuroru reached back, grabbing the sheets for dear life. Her stocking-clad legs bucked and bounced against the mattress as she got the much-needed dicking she wanted. The two were nearly naked, clothes strewn about her suite as she’d literally thrown them back onto her bed.

“F-Fuck!”

This wasn’t even the tweth curse she’d let out. Gray quickly learned just how coarse Kuroru could be when she was finally free of the ‘doting mother’ side. He was starting to see the infamous trainer that had trekked and slept her way across Unova...and she still had. “C’Can’t believe you waited this long.”

The MILF rolled her hips as she tried to respond. “What, did yo-oooh-u think I’d lead you t-to a baaaathroom? Or a-a-a closet?”

She reached up and slammed his head down between her breasts. Gray got to work and licked her cleavage, reaching all the way up to her collar. “Ooooh...B-Been there, fucked that - bed’s better.”

Every coarse word and evocative admission made his dick hard in her gushing pussy. Somehow, despite all the numerous claims he now believed, Kuroru was still tight - almost unbearably so. “Arceus...you really are a whore.”

She didn’t even try to sound outraged at his accusation - she’d already owned it years before. Instead she simply grinned and taunted him, “Damn right...and Y-you’re not le-eeeeeee-aving until you pump a baby in this sluttty mommy~”

Gray’s eyes widened. “K-Kuroru I thought you were-”

The MILF cut him off by wrapping her supple thighs around his back. Her nails reached around and dug into his back as she hissed, “Stop talking and let’s find out - now cum you bastard!”

He reached for the head board for much-needed support. Kuroru’s tight twat was threatening to suck him dry...actually, it almost felt like it was going to break his cock off. “FUCK! H-How are you this tiiiight?”

Her response was to reach up and latch onto his neck. “Mmmph, mmmmph”. Her loud, lascivious suckles and bites were quickly drowned out as really started jackhammering her. His payback came as her clit slammed against his crotch. “FUUUUUUUUUUUUUCCCCCCCCCK~”

The soundproof walls rattled as the two came. The bed groaned pitifully as they pounded out their lingering frustration, even as he pumped sticky, potent cum deep in her snatch.

The two went limp as he collapsed atop her. Kuroru squeaked, but made no move to protest, especially not as he was pumping her womb full of baby batter. Her wrist fell back and accidentally knocked the lantern off the nightstand.

_ Crash!. _

From the darkness, her satisfied yet hungry voice called out, “N-Next time, we’re ordering out -got it?”


	9. Shiri

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

The lounge was almost dead silent between breakfast and lunch. Everyone that's been there earlier was out on the golf pitch or the other accommodations, and the staff had stepped out after confirming that the special case was still there. 

Gray was honestly stunned, leaving his coffee to cool beside him as he gawked at the nonplussed older woman. Her cavalier admission had left him numb.

She knew - somehow, someway, this woman knew what he once was...and she didn’t seemed fazed in the slightest. “Kid, trust me - once you’re in, you know when others are as well. Doesn’t matter what region or what you fall under.” she shrugged 

Shiri - no connections, no accolades, but somehow she wound up getting signed into the Nidoqueen Package regardless. Lusamine had been rather tight lipped about what the Unovan MILF’s background entailed, and simply told him to treat her as just another cherished guest, free to any accommodation or service he could provide.

Especially himself.

Gray tried to think of what to say in response. “So which one?”

She set down her half-full mug before answering, “Plasma - doing that whole ‘free the Pokemon’ idea that sounded good on paper. Obviously the higher-ups were...well shady, but there were some of us that wanted the lie more than the truth.”

“Are you still...connected?”

Shiri shook her head. “Not anymore- it split up and we all scattered. Some of us didn’t like learning what the true purpose of our family was for, and cut out losses to find a new life. A new family.”

Gray said nothing as she sipped her coffee more. The way this woman so casually admitted to her own seedy past was...striking, to him. She finally set the cup down and offered a gentle sigh. “I was lucky to already have one.”

“Your daughter?”

A smile graced her lips as she gently nodded. “She’s the light of my life Even got her mother the full bill for this little shindig...speaking of-”

With a snap of her wrist, her Xtransciver was active and ready. Shiri’s fingers were swift as she continued to bore down on him with her now-sultry gaze. She’d gotten that off her chest, and now she wanted to indulge in her benefits. “I Think it's time to collect, don’t you,  _ Nidorino _ ?

_ Beep! beep! _

“M-Ms. Shiri - the other staff will be back soo-”

Gray’s protests were cut off by the MILF’s hungry lips. She grabbed his vest and pulled him in deeper, leaning across the table until her ass was in the air. A hand reached back to seize his shaved head and force him closer until he could barely breathe. He was utterly at her mercy - unable to muster a single defense against her wicked tongue.

His vision was already blackening when she finally let him go. The two panted heavily, letting the bridge of spit break between them. “...Better make it quick then, huh?”

* * *

_ ‘Pwah!’ _

The MILF pulled away and sucked down gulps of air. Shiri paused long enough to toss off her shirt completely, letting it land against the table. She let her hips roll, keeping him nice and hard against her moist pussy. “Hah...Hah...y-you’re good, kid.”

Gray didn’t say a thing, not when he was hypnotized by her nice, fat tits constrained by a rather plain white bra. Shiri reached back and unhooked her underwear, letting the cups fall on his chest. “But let's get to fun-  _ now~” _

The MILF adjusted herself atop him until her plump, covered ass was in his face. She unzipped his pants and fished out his cock. “Mmmm~”

He took the hint and pulled down her pants, exposing her simple panties straining between her globleous rump.  _ ‘White...how unexpected.’ _

Shiri felt his gaze on her barely covered loins, making her cheeks burn. She leaned down and took a nice whiff of his musky dick. It was different than the aroma of coffee, but no less mouthwatering. Her tongue lulled out and gave it a nice, long taste.

It was risky - anyone could walk across the promenade and glance in to find them going at it on the bench. It may be hard to see who it was exactly, but the act itself would be plain as the clear skies outside.

Gray rolled down her panties, leaving them around her thighs with her pants. His goal was already in sight - her sweet, succulent, and utterly  _ gushing _ pussy. Just staring at those puffy lips were making his mouth water...and he made sure to show her that in kind.

“Nngh! Y-You’re not wasting time,” she gasped again as he feasted on her fertile flower. She felt the wet slaps against her twat. She decided to mask her squeaks by popping his crown in her mouth.

Sixty-nining in the middle of the resort’s lounge, in blatant view of the wide, uncovered windows. The Nidoqueen Package allowed for such an accommodation, but didn’t mean they were free of any potential risk. The ever-looming threat of being caught was clear in their minds...and it was arousing as hell.

Shiri focused on bobbing her head and trying not to wince with every lascivious twitch in her snatch. Gray’s enthusiasm spurred her to match his pace. His eagerness wound up causing his jaw to graze against her clit.

_ “MMMMMMMMMMMMMMMAAAAAAAAAAAAH!” _

Shiri’s gargled screams rocked his dick and triggered his own climax. Her juices assaulted his face and covered him in a mask of sin. Her throat was painted white as thick cum threatened to choke her. Some cum actually wound up shooting out of the MILF’s nose and struck his crotch.

Gray’s head hit the bench with an alarming  _ thud _ . Shiri coughed out spunk on his lap as she gasped for breath. “huh...huh...huh...guess the fun’s over?”

Her answer came in the form of an errant spurt landing against her eye. The MILF winced and quickly grabbed his dick to prevent any more shots. Her lips arched up into a devious grin.“Mmm, maybe not.”

She gobbled him up again, keeping his shaft in place as he shot more loads in her outstretched cheeks. Her young lover was a bit too addled to properly return the favor, but she didn’t hold that against him. Not when he was providing her with a hearty helping of hot, salty cum.

Shiri finally pulled off with a loud  _ pop _ , leaving only a thin strand between her lips and his dick. She turned back to him, tounge cleaning the remnants from her lips as she cooed, “I’m up for another round if you are...my room?

Gray managed to shake off his stupor in time to respond. “I think...There should be a service elevator close by…”

* * *

_ Click. _

Shiri didn’t even let Gray out of the entry hall before slamming him against the wall. Her head tilted up as she desperetly sucked his lips and goaded his tounge out. He dropped the napkin hiding her bra and left it at their feet.

They weren’t in the short hallway entrance of her suite and were already back at it. A perfectly good couch or chair was just a few feet away...and they were already plugged and pinned just past the closet. 

The MILF found their roles reversed as he twisted them around. Her pointed nipples poked against her thin shirt as she bucked and rolled against his lap. His hands roamed up and down her shapely hips, admiring her motherly curves. Her ass rippled and slapped on the wall with every thrust.

Having a distinct but similar past meant they had familiarity with the concept of brisk, confined copulation. Gray actually had to refrain from throwing open the closet and pushing her in - old habits die hard after all. For her it was much easier since her mouth was occupied with his.

The two broke away, gazing with lidded eyes. He reached up and gently cupped her breast through her thin shirt. His coarse thumb rolled over her erect nipple and sent a shock through her body. “Ahh~”

Shiri’s eyes widened before muffled herself with her own teeth. He eyed the way she bit her lip and resisted the urge to laugh. “We’re not in the lounge anymore -feel free to be as loud as you wish, Ms. Shiri.”

The MILF bristled at his remark, but reluctantly let her lip go. Her cheeks were threatening to ignite as she mutter-moaned, “Y-Yesss...o-of course.”

Shiri had a hard time mustering up the drive to act so...shameless, even in her own bedroom. She simply wasn’t  _ that _ kind of woman. Still, she tried to follow his advice by letting her hands wrap around his neck and away from her mouth. Gray responded by reaching back to cup her rear as he kept thrusting.

The duo fucked with no shame or regard for their surroundings.The suite’s walls may be soundproof, but being this close to the main door wasn’t going to mask everything. Anyone that was passing by could easily hear the rhythmic thumping and wet slapping, clear as day. Gray’s rumbling grunts could also be heard, less so for the MILF he was entertaining.

His cock reached a particularly erogenous spot, eliciting her leg to grind against his. Shiri’s head was smashed against the wall and threatening to come undone. Sweat kept her shirt pinned against her body and clung to her like a heavy skin. Between her breasts, crotch, and even the electrifying friction of thigh on thigh pushed her over the edge.

“Ahhh~!”

Gray slammed into her one last time before unloading rope after rope of hot, sticky cum in her deprived womb. Their shaky legs buckled and collapsed, sending the two of them down to the floor as they rode out spine-numbing orgasms.

After some form of eternity, the MILF finally came back down. The dull buzzing on her wrist was like a gnat that she struggled to ignore. Shiri’s eyes fluttered open and glanced down at Gray. “Y-You know, if you ever need someone to talk to...I’m all ears.”


	10. Hope

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

“Oh, this feels nice…”

The MILF happily cooed, floating in the pool on her back. Her shapely, motherly body squeezed into a tight one piece that hugged her. A sturdy inflated lounger left her drifting in the spacious waters. Soft, cooling morning rain sprayed down on her as she relished the rare opportunity efore her -having the pool to herself, by sole virtue of being out in the rain.

Hope - mother of Trial Captain Lana. mother of three, happily married to a peerless fisherman...and horny as hell.

Gray wasn’t even shocked when he walked into the abandoned patio and saw who was waiting for him. There wasn’t really any room to be surprised with this arrangement anymore. All he needed to do was offer that winning smile and bow. “You called me, Ms. Hope?”

The MILF turned to him and grinned - not even hiding her coming intents. She reached over and quickly fiddled with her thankfully waterproof Xtransciver. “Yes...I was wondering if you’d care to join me,  _ Nidorino~?’ _

* * *

_ ‘Mwah. mwah. Mwaaaaah~’ _

Hope’s lips drew up and down his cock, introducing him to the wonderful contrast of her hot mouth and the cool pool water. She felt his fingers coiling into her flowing hair as she sucked him off underwater. Years and years of swimming and  _ training _ had left her with an impressive lung capacity...and an even more impressive appetite.

Her and Maiya had an arrangement, based only on the fact he was gone so often. She’d get to indulge in whatever taste she wanted - local or foreign, and in return he’d remind her what she still had as soon as he got back. She opted for some nice tourists just to keep things from getting awkward, and even then didn’t partake quite as often as she could.

But here at the Hano Grand, opulence and indulgence was the name of the game. And she was ready to play.

Gray grunted as he struggled to endure her incredible, underwater fellatio. “M-Ms. Hope...are you okay d-down there?”

Her response was an ok sign sticking out of the water before it slipped back beneath the surface. This wasn’t even the deepest she’d ever given head - or the longest for that matter. Still, she was aware that the rules restricted her time and wanted to get something more than just an early morning snack.  _ ‘Brace yourself kid - tide’s coming in~” _

Hope pushed forward and sent her lips crashing into Gray’s crotch. His ass hit the side of the pool as she literally sucked the cum out of his balls. Her already slick twat was practically gushing as she felt his nails dig into her scalp.

_ Ulp Ulp Ulp Ulp… _

Gray fought away the stars in his sight and came down from his orgasm. The cool rain felt extra refreshing now as he enjoyed the MILF’s tight throat. He glanced down at her closed eyes, slightly distorted by the rippling water.

_ Splash _

Hope’s head broke the surface shortly after leaving his flaccid dick. He noticed her billowed cheeks and was ready to question her...only for her to simply open her mouth and show the impressive amount of spunk bubbling between her teeth.  _ ‘Aaaaaaa~’ _

Her gargles made the churning slurry of spunk ripple like waves. He saw her tongue breach the surface like a pink wailord before crashing down into the milky, bubbly sea. His private gaze into her mouth was cut short as she closed her lips, swallowed, And showed him her mouth again.

Not a single drop remained.

The MILF licked her lips clean before breathily saying, “That was good...but I want more you know~”

_ ‘Of course she does’ _ he shook his head clear and tried to stay professional. “Shall we find a lounge chair, Ms. Hope?”

Hope brought a finger to her cheek and made a show of pondering. One look in her shining eyes through the misty rain made it clear that it was all a farce. She glanced at the discarded floating chair at the other end of the pool. “Hmmmm...I was thinking something a little...closer.”

Gray bit back a groan as he reluctantly complied. Hope was already underwater and swimming to their destination He watched the way the water rippled across her tight, globelous cheeks. He rushed to join her, not at all caring that he’d left his uniform behind.

The Milf surfaced on the other side of her chair with a big grin. The floats in the pool were remarkably durable - at least strong enough for two grown adults to lay on. She was planning to test that.

He made it over just as she pulled it into a more shallow end, near a set of stairs into the pool. “Took you long enough,” she teased him from across the lounger. Hope rose...and showed off her bare breasts and revealed pussy.

Gray gawked at her brazen state, effectively naked in a public pool in the middle of a soft morning rain. “Well, don’t just stand there...help me on, Nidorino~”

He guided her, enjoying a nice cop of her plump rear in the process. He made sure the MILF was nice and reclined on her stomach before joining her. The lounger sunk a little, but stayed floating and upright.

“Mmmm….”

Hope cooed as she felt his naked, hard cock rubbing against her ass. He loomed over her, placing his mouth against her ear. A sudden idea came to Gray and he whispered, “Have you ever had it  _ dirty _ , Ms. Hope?”

The MILF squeaked, especially when he reached down and groped her breasts. “N-Never. I-Ah!-I’ve never been fucked in the ass in the pool before…”

Gray bit back a chuckle at her odd admission - Hope was a  _ terrible _ liar. “Would you like it?”

Hope squirmed beneath him and whimpered, “I-I shouldn’t...wouldn’t that be rather foul of me?”

The way she said it and the way her hips made it clear. Gray’s rumbling voice thundered in her ear. “It would indeed.”

He stuck it in.

“Ngh!”

The MILF gritted her teeth as she felt him invade her ass. His cock was much much longer than her husband, and nearly as thick to boot. The way he was stretching her colon out was different than she was used to. “Hah...S-Slow down, kid.”

Gray tsked, but reluctantly obeyed. He was already halfway in her ass, and there was no telling how much time they still had. Still, this was a fantasy for the guests, not him.  _ ‘I’m just getting paid to be here - enjoying this is just a bonus.’ _ he shrugged.

Hope squirmed back, taking more of his dick in her ass. She eventually felt his balls flop against her twat, denoting that she was at the base. He let her decide when and how fast they’d actually start, even knowing that they were on the clock.

The MILF started slow but quickly picked up her pace. Her fat ass rippled and clapped against his crotch with every thrust. She felt his long, thick cock squeezing and rubbing her ass. Her untouched snatch was already glistening with desire. “Oooh, that’s it~”

_ Pap pap pap pap pap _

The patter of rain droned on as it mixed with their sweaty bodies. She squeezed the edge of their floating lovenest, feeling the cool, salty pool water on her manicured nails. Her shapely thighs pinned against the solid armrests of the lounger, keeping herself in place just in time as a sharp jolt threatened to escape her lips.

Thinking fast, Hope bit down on the lounger’s edge to mask her moans. Ordinarily this would be a good call, but right now it presented another issue for Gray - one more to pile on the rest of this encounter.

Her teeth were digging into the wet, spongy material. She was damaging hotel property, which was heavily frowned upon. Pulling her off would risk taking a chunk out of the float, so he’d have to be a bit more creative first.

Gray’s hands roamed away from her hips as he kept thrusting. Her locked limbs kept the two in place above the thrashing float. He guided his hands in opposite directions - one going up to her nape, the other around her stomach to rest between her legs.

Hope mewled in his grasp as he began a two-fold massage. His fingers rubbed around the top of her snatch, lightly caressing her hooded clit. His other hand busied itself with gently stroking her slender neck.

The MILF’s eyes rolled back under his ministrations. Her jaw slackened, leaving a puddle of spit where she’d bitten down. As soon as her teeth were free, he pulled her up by her neck in a firm grasp before shifting to seize her hair.

“AAAAH!”

Hope’s mouth hung open and filled with cool, refreshing rain. Her lustful moans came out gargled as his fingers massaged her scalp. Her wanton hips kept undulating and grinding against him. Gray leaned in and whispered in her twitching ear, “Are you ready, Ms. Hope?”

_ “Y-yessssssh.” _

Gray reached down and jabbed her clit between his fingers.

_ “AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAARGGGGRAAAAHHuuuuuuu...” _

Her orgasmic scream was silenced by the pool fistful of water sloshing and gurgling in her mouth. Her nails dug into the lounger’s edge until it was forced under the pool’s surface. Her young lover slammed into her ass one last time, pounding rope after rope of sticky cum in her butt. A fountain of quim blasted out of her snatch and drizzled into the pool itself.

Gray winced - the cleanup crew was  _ not _ going to be happy about this one. Still, he couldn’t dwell on the opinions of Pokemon that already despised him, not when he had a job and a hot Alolan MILF to do. Or rather, keep doing.

She felt his loads dwindle to nothing and leave her tight rump sloshing in cum. The MILF’s fingers loosened against the inflatable lounger, leaving only the little pricks where her nails had dug out some of the chair’s material. His still hard cock twitched, jerking her out of her lustful stupor.

Hope turned back with a mischievous grin. I think I need a bath after that~”

* * *

“Oh oh ohhH! T-This isn’t what I mean-nnngh!”

Gray’s fists on her tits cut her short. His cock slapped against her rump cheeks as her tight twat slurped his shaft. The freshly prepared bath remained utterly untouched as the two fucked against the counter.

While Lusamine’s instructions had been drilled into his skull, Gray had a certain limit to the whims of the MILFS. Besides, his main focus was on their pleasure. It certainly didn’t have anything to do with a near slip in the baths back at Po Town...not at all. “Ms. Hope, I’m just ensuring that you properly enjoy your bath - that’s all.”

Hope grunted, unable to truly respond. His hands were busy roaming and rubbing her supple bare body, reaching up from her nipples all the way down to her erect clit. Her disappointment was quickly washed away as he did his best seeing to her body’s every need.

The MILF really,  _ really _ wanted to get fucked in a bath like she always got at home. The spacious tub was giving her all kinds of fun ideas that now were squandered. Still, an all expense paid trip to a luxury hotel, with the bonus of getting plowed whenever and wherever she wanted...hard to feel disappointed, honestly.

Hope’s boobs pressed against the mirror. Her heavy pants fogged the glass as she tried to shake off the early morning haze. Her toes curled around the lip as she struggled against him. Her loins brushed against the edge, mistakenly jabbing the lip against her erect clit.

“AAAAAAH!”

Gray growled as her already-tight pussy clamped down on him in orgasmic throes. His cock throbbed and erupted in her twat, pumping wads of hot cum in her unoccupied womb. Her head tapped against the mirror, leaving a swipe in the foggy layer. The two stayed hunched over the sink until the last trickle was coaxed out of his dick. Gray’s limp shaft plopped out, causing her to drip on the counter. 

He recovered faster than her and gently picked the MILF up before guiding her to the waiting bath. Gray let her shapely body sink into the sudsy water, making sure her neck rested against the cushion. Hope cracked her eyes open and smiled.

“Y-You ever been on a Sharpedo? I’d love to take a ride sometime~”


	11. Sima

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

* * *

“Fore!”

The ball whizzed far in the distance thanks to her powerful stroke. The duo watched it land before she pumped her fist in triumph. “Oh yeah! Getting better every swing!”

Gray aired out the polo shirt and bit back a grumble in the heat. “That’s very true. Though perhaps next time you should aim away from the sand barge, Ms. Sima.”

“Eh, details.” she scoffed before walking over to wear her ball landed. She casually reached back and pulled down her short skirt. Gray bit back a groan of disappointment and focused on the firebrand MILF he was caddying for.

Sima - Mother of the Trial Captain Kuwae. She usually spends her time on the family ranch taking care of Pokemon, but her wonderful husband and son had chipped in to earn her this all-expense paid little shindig. Way she figured, it was worth getting as much done as possible that she otherwise wouldn’t do. Like Golfing.

Hence why he was here, split between being a dutiful caddy and a shameless voyeur. Perhaps wearing a tennis outfit wasn’t the best choice, but he certainly wasn’t going to complain. Not when he had the welcome sight of her bare, bronze arms and two nice, plump, rich reasons to keep his thoughts to himself. _‘Not really sure what the standards are for wearing a thong on the pitch...but I’m not gonna be the snitch to re-write them.’_

Sima wiped her brow. “Geez, it's like we’ve got the whole range to ourselves, huh?”

“You’ll find that things are a bit more active here than the ranch, Ms. Sima,” Gray insisted. It was an automatic response that’d been drilled into his skull as he kep up this charade of being on the hotel staff. The heat made him less keen to actually try and make it convincing, and it showed.

“Mmm, could’ve fooled me,” Sima chuckled. She descended into the sand trap to look for her ball. Gray followed her, thankful for the slight shade offered by the incline. He wiped his forehead clear and adjusted to the dimmer light.

“Where do you thi-” he trailed off as he got a load of what was before him.

Sima, already down in the dirt on her hands and knees. Her skirt hiked over the top of her ass and her thong shoved aside. The MILF glanced back with her ponytail draped over her bare shoulder.

“You know, speaking of fooling…” She grinned before tapping her Xtransciver.

_Beep beep._

“Well, _Nidorino_?”

* * *

“Uh uh uh. U-ooooh, that’s it~”

Sima’s fists tightened around her golf club as she leaned forward for support. Her bare knees were already covered in sand as she rocked back and forth against Gray’s pistoning cock. Rippling dark cheeks clapped and jiggled with every wet slap.

He watched her bronze, bare back drenched with sweat with her top pulled up to her armpits. Her bouncing tits trapped in a compressed sport’s bra was making a tempting case for forgoing her shapely hips and giving those udders some loving instead. He reluctantly compromised for her silky shoulders.

“W-What are yo-ooooh, that’s good.”

The MILF melted against his fingers as the jostling and bucking transformed his grip into a deep massage. Gray wouldn’t claim to be an expert, but his boss had insisted he learn the basics, with herself as a willing subject. Sima certainly didn’t mind the extra effort.

“Not bad, kid - Been aaaages since I got a mas-ssshiit!”

Sima’s praise was cut off as he slammed into her twat. His thrusts shifted into hip rolls as she massaged her velvet walls with his cock. The MILF cooed in bliss at this perfect little moment.

“...I don’t know man - doubt they’d be into it.”

The two froze mid-thrust at the muffled sounds above. In their lust they’d missed the warning sounds of another pair of golfers coming up to the pitch and playing through. It was sheer luck that no balls had landed in the large sand trap and exposed them.

“Oh come on bro - we’re talking what, a dozen horny ass MILF cooped up in a luxury hotel with their husbands far far away? Tell me they aren’t dropping their panties right now to some lucky bastard.”

 _‘Well, he’s not exactly wrong.’_ she silently grumbled as she thought of Rango out traveling for the ranch. His anniversary gift for her turned out to be a one way ticket to getting all her pent up needs handled. And she was eager to see it through.

Gray bit back a curse as he felt Sima’s pussy suck his cock up again. The MILF was keeping her pace slow enough to be silent, but quick enough to send sparks up his spine. Agonizing minutes passed between them as they tried to keep their romp quiet.

“Look, are you going to keep fantasizing about these married women, or are you going to play?”

“You’re just pissy that the hot director from Aether is already gone.”

“T-That’s bullshit!”

“Suuuure, and I’m sure you’re not dreaming of ripping off those glasses and-”

Sima groaned in frustration at the banal banter as it trailed away. The thirsty MILF almost cheered when the pitch was finally silent again and was eager to finish off before the next distraction came up. She reached up and bit her top’s collar to silence herself.

Gray saw her action and took a chance. He reached up to her hat and shoved her face into the sand. The brim of her visor kept the sand out of her eyes and mouth as he _really_ began to rail her.

Sima’s screams and spit soaked into her tennis dress. Her bare breasts dug into the sand and tickled her pebly nipples with little hot grains. It was all too much for her. “ _FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFPPPPPF!”_

Cum blasted out of his cock and into her greedy womb. The force of his eruption blasted out around her plugged twat and guzzled into the sand. Gray’s head felt light as he collapsed against the hot rancher.

Sima spat out her ruined dress and drooled into the sand trap. Her throbbing forehead was heating up in the hot sand, while her mostly bare body was almost cooking in the blistering sun. She was used to doing ranch work in the tropical heat- hell, she even did it naked sometimes.

Gray pushed them on their sides before finally pulling out. The MILF glanced over her sandy, sweaty body and grinned at him. “Heh, you look like you took a dive off a Tauros.”

“Yo-Yo-You’re not looking much better, Ms. Sima,” he fired back. His lethargy made her laugh before she crawled over to him.

“Yep - back to my place now?”

* * *

“HAH! HAH! F-FUCK, THAT’S IT!”

Sima’s screams echoed in her suite’s living room as she writhed on his cock again. Unbound hair clung to her sweaty, sandy skin. Her shapely legs rippled as she struggled to hold herself up. Her nails dug into the ottoman as she pushed it against the matching chair.

Gray’d managed the impossible - Guiding her through some employee passages and up the elevator had miraculously gotten them back to her suite without issue. Her dress was already off and thrown on the couch before she’d bent down over the foot rest. The sight of her black thong almost buried in her rich, dark ass was too tempting to pass up.

His hands dug into her ass and left deep indents. Wet slapping filled the room before the heavy stench of sex threatened to choke them out. Neither one really cared, least of all the lucky ex-con. “D-Damn you’re tight.”

Sima growled back. “Heh, p-perks of the ranch kid. You ain’t seen nothing yet.”

He barely heard her taunt before her already-tight pussy almost broke his cock in two. His head tilted back. “FUCK!”

The Milf smirked in triumph. “T-Trust me - you need th-eeee-se to break a Tauros in.” She emphasized her words by rolling her ass against his lap.

_‘Arceus sake this woman’s a demon!’_

Gray shook off the temptation to nut and focused on the crafty MILF. his hands adjusted until they were pushing down on her back. Sima hissed as she was slowly but surely pressed down on the ottoman until her tits were caught between knees and the seat. He kept forcing her down until her knees finally bent beneath her and relaxed her dangerous thighs.

It was time to _break_ the bull-breaker.

Sima purred in delight at his forceful treatment. Tears streaked down her cheeks as she reveled in utter bliss. He was finally treating her the way she wanted to be treated, the way her husband would never dare to no matter how much she begged.

Rango was never going to treat her like the horny cow she was. The kind of sow that wanted to be bred and left with a big belly and fat, milky tits.the perverse thought meshed perfectly as Gray’s dick forced cheek into the cold cushion.

“FUCK! I’M CUMMING!”

Her shriek thundered in his ear as he struggled to thrust in her vice-tight pussy. Her velvet walls choked his dick and taunted him to blast out every drop of man-milk he could muster for the ripe, naughty sow. And he gave it to her - all of it.

Sima drooled on the ottoman as her twat was pumped full of cum. Hot, sticky, syrupy cum that bubbled and crashed against the cool seed still sloshing in her womb. Her shaky knees finally collapsed under her as her lover pulled free and left a parting shot across her ass.

Gray stumbled back and collapsed on the couch over her dirty dress. He watched the syrupy trails of spunk bubbling and oozing out of her dirty snatch. Sima glanced back with a tired smirk. “Come by the ranch one day, and I’ll show you how _real_ animals fuck~”


	12. Delia

* * *

**All MILF art thanks to the supremely talented[Take-Cha!](https://www.pixiv.net/member.php?id=3051326)**

* * *

**_I have a discord now! Come on over to[The Steakhouse ](https://discord.gg/rPhkz4G) and join us. See you there :)_ **

“I’ve worked something out - it’s not about the title anymore.”

Gray glanced up from his wine at the lovely lady he was sharing the banquet with. Out of everyone in the Nidoqueen Package, this woman seemed to have among the most clout. If nothing else she seemed to simply know everyone already. And thanks to the hot little black dress that easily showed off smooth, stocking-clad legs and supple thighs, it was clear she was among the best of the beautiful breed.

Delia Ketchum

He tried to focus on what she was saying over the bustling around them. Their table was thankfully rather isolated, but still close enough to see the stage and screen. The platitudes were already done so now all that was left was to watch the show. “How do you figure, Ms. Delia?”

The MILF giggled before taking a sip of her own wine. Her lipstick left a clear mark on the once-clean glass as she smacked and savored the taste. “My son’s been traveling for years now - he’s gone to so many places and met so many wonderful people, done so much more than anyone else in our sleepy little town.”

She leaned in, looking him right in the eyes. “Tell me something, Gray - what does being champion get you?”

_ ‘All the money and hot tail you could want.’  _ “I’m afraid I won’t be knowing that anytime soon, Ms. Delia.” he shook his head, keeping his gaze on her face and not the bounce of her tits.

“Responsibility - restrictions and regulation, with the eyes of the world on him. Maybe that’d suit him, but somehow I have my doubts.”

So he keeps his profile low, even loses a few matches in the new region. Builds up some young and promising trainer and sets them on their own path. Relive the same magic he’d had on his very first journey.”

Gray mulled her outlook and simply couldn’t mesh.  _ Lady, I don’t think your son is actually as good as you make him out to be.’ _ “That seems...optimistic”

Delia shrugged “You’ll just have to see for yourself,” she mused. Gray watched her take another swill of her wine, lazily cradling it with one hand.  _ ‘Wait, where did her other hand g-” _

_ Beep Beep! _

The MILF smirked before glancing down to his wrist. He cautiously flicked it open and checked the message inside.

**_Enough banter - whip it out, Nidorino._ **

* * *

**Keep watching.**

Gray reluctantly obeyed and watched the utterly dull battle on screen before him. He may have been an old skull, but that didn’t mean he found Pokemon battle particularly exciting. Not even these trumped up spectacles were really holding his attention, though this time he had an excuse of having to look away from a drop dead sexy MILF as she stroked him off under the table with her feet.

brrp

Gray glanced down at his Xtransciver and pulled up the message.  **So how does it feel? Like them?**

“Ahem”

He looked back up at the battle and sloppily tried to type out a response.

**They’re fantastic - Kalos?**

Delia laughed, a clear, bubbly chortle that sung through his soul and into his twitching loins. He felt her catch him in the stocking-clad gap between her toes before she easily responded,  **Yes, actually. Imported them myself.**

She put some emphasis on her foot pumps, really selling him on the sheer quality of the Kalos-made leggings. It was like he was getting kissed on his cock, with just a tiny tinge of static jolting through his shaft. He leaned into her touch, still trying to watch the pointless battle on screen.

Ziiip

Gray flinched as he felt the metal tag catch on his crotch. Delia managed to navigate around it and loosened his pants completely. Her foot reached in and prodded out his dick, letting it stick out under the table.

**I want to see it.**

Delia’s demand flashed across the screen. Gray tried pressing his luck and posted back,

**It’s down there waiting for you.**

His witty retort made her smile, but she still shook her head.  **I’m enjoying the battle - show it to me.**

It took a moment for him to realize what she meant. The nervous man glanced around to make sure their fellow banqueters were watching the battle before slipping his wrist under the table.

Brrp

Delia leisurely took a sip of wine, still focused on rolling her nylon-clad toes over his shaft. Her other foot reached higher and began to prod and tap against his glans. The MILF finally set her wine glass down and lazily glanced at the now minutes-old message.

Gray struggled to swallow down a piece of meat to distract himself. He heard her give a low whistle of appreciation, cleverly masked by some loud cheering as someone’s Pokemon fainted on screen.  **Oooh, that’s nice. For me?**

He got another idea in his head and tapped back, **It could be, if you’re willing to share something.**

Delia’s smile widened **And what might that be?**

**Show me your breasts**

**How crude :(**

The face on the screen simply didn’t match her beaming grin. She looked around for a reasonable distraction, still pumping him off with her feet. Gray resisted the urge to buck his hips up and tried to endure his torment.

FAINTED!

A loud roar went through the banquet as the challenger went down for the count. Delia used the distraction and quickly whipped out one of her tits, letting her dress hang open in her cleavage crack.

Click!

The MILF was stunned as a small flash went off from his wrist. Gray offered his own triumphant smirk as he turned the screen towards her, showing a perfect capture of her planned wardrobe malfunction.

She scoffed and drank more wine before tapping back,  **Oh you are devious. I like that <3**

Our next Challenger, hailing Aaaaaalll the way from Kanto-

Delia’s feet froze, trapping his twitching dick between her soles. Gray’s grumbles barely registered for the excited mother. “That’s him - that’s my son!”

Gray shook off his frustrations and watched the clearly grown man strolled onto the stage with pride. A certain mouse type pokemon perched on his shoulders as he waved to the audience. “He looks...old.”

Delia giggled, a little too sweetly. “Well, he has been doing this for a few years now

So how long would that-”

“Ahem.”

Gray’s question died in his mouth as he went back to watching the match at hand. The whole time he could feel her nylon grip on his dick, never really moving and simply holding him in place.

Delia watched her son’s battle start, eyeing him with the same keen eyes that have watched hundreds of battles before. Her feet stayed in place around Gray’s cock - never moving for what felt like an eternity.

Finally, her feet started moving again. He let his appreciation be known thanks to a low groan. The saucy MILF across from him snickered before pulling her Xtransciver back out. **Oh wow, you feel tense.**

Gray sneered at her coy banter and jotted back,  **You left me waiting**

Delia read his message and mock-pouted. He didn’t miss the way her kissable lips morphed into an almost perfect O - just the right size to take something in her mouth.  **Poor baby. How can mommy make it up to you?**

**Why don’t you go check on it?**

She pretended to mull his suggestion before shaking her head.  **Mmm, but then I’d miss his match.**

**“I could record it for you**

Gray’s desperation was clear on his face and his words, much to her delight. She tapped her cheek with a finger as she watched her son’s little gamble before brightening up. **I have something else in mind :)**

Her feet pulled away, much to his irritation. He glared over at her, only for her to wag her finger and jot down,  **Keep watching - you might learn some things.**

Reluctantly, he obeyed her command and focused on the exhibition battle. After several minutes he was ready to simply leap over the table and take the MILF on the carpet. The only thing he learned was that he was pent up as hell and ready to burst.

_ brrp _

His Xtrnasciver buzzed a mere seconds before his hips tensed back. Gray shook away his wreckless impulse and slipped open the screen. “Holy fu-”

KNOCK OUT!

She certainly was - there before his eyes was a perfect view of one of the most perfect sets of pussy lips he’d had the pleasure of seeing. Thick, plump and ripe, pried open by a pair of fingers and showing the glistening walls within. He noticed the hood hiding her clit nearly obscured by her wrist, along with the decent sized trim patch of pubes. It was too dark to accurately make out the color, but he safely assumed the carpet matches her drapes.

A new message overtook the picture as Delia started going for the kill. **I’m gonna take you back to my room after this, and you know what we’re going to do?**

He didn’t even have time to playfully ask before her feet were back on his cock. He felt those nylon toes furiously jerking him off now. His focus was utterly shot and he couldn’t even pretend to watch the battle anymore.

Luckily, Delia was done with that farce and wanted him as riled up as possible. Another message popped up

**We’re going to fuck, young man - F. U. C. K. As long and as hard as you can last, whenever and wherever I please.**

**And we’re gonna start as soon as you finish. As soon as you cum and stain the table with your spunk, I’m taking you back with me. And I swear you’re not gonna be leaving until I SAY you can go.**

Her harsh rhetoric rippled through him and undid the last barrier of restraint. Gray chomped down on a cold piece of beef as she came in her toes. Her feet didn’t even managed to block a single load, and soon her stocking-clad toes were covered in sticky white spunk. Delia didn’t seem at all ashamed or even aghast - not as she kept vigorously rubbing him off and smearing more of his seed between her toes

Delia pulled her feet back and blindly wormed for her discarded shoes. She ignored the muffled squelch as she stuffed her sticky toes back in her heels. The MILF simply removed her napkin from her lap and made to rise. “I think that’s enough for the evening.”

Gray was busying himself with pushing his cock back in his pants before he glanced up at the saucy woman. “Not going to finish watching?”

“No need - He’s going to win. I can tell.”

He finally had to bluntly ask. “And how’s that?”

Delia finished her wine and set the empty glass down. She walked past him, her head barely coming up to his chin. He watched her plump, kissable lips crack open with a smile as she simply declared, “Simple - he’s not done enjoying himself. And neither am I~”

And then she was gone - making for the door away from the captivated audience. Gray didn’t even spare a glance back as he snuck off to follow her, eyes shifting between the mess at her feet and her nice full ass jiggling with every step.

“Go, Pikachu!”

* * *

_ Fzzzzzzzzzzzzzzzzzzzzzzzz _

“Mmmm, that’s it - right the-eeeere~”

Delia cooed in delight, squirming against the foggy glass. Her nails tapped against the shower walls as she happily took a nice, hard cock up her supple butt. She glanced back at her young stud of a suitor and licked her lips. “Y-You didn’t even waste time, did you Nidorino?”

Gray’s answer was to smack her ass, letting a loud crack echoed over the water’s hiss. The MILF yelped in delight as her fingers scraped against the glass. “Aah! T-That’s the spot!”

He repeated the action, alternating between grabbing her hips and slapping her rump. Their hips smashed together at a frantic pace, helped along by the lubrication of the shower. Whatever scruples he had about fucking and slipping had been abated as she tossed in the dry mat before sprading her cheeks.

Delia arched away from the glass before he pulled her roughly back by her shoulder. Her wet hair smacked his cheek as he reached into her panting mouth and stuck his thumb between her teeth.  _ “Arrrrh, shooo guuu~” _

Gray smirked at her babbling before reaching between her legs and fiddling her throbbing clit. She was putty in his hands as he attacked her from all holes. “AAAYM C-CUUUUUUUMMM!”

Her juices splashed against the glass and left a noticeable stain. The MILF buckled forward until her nose tapped against the wall as her senses all burned out. Gray collapsed against her as wad after wad of sticky, potent cum blasted right in her ass.

Delia and Gray shuffled down until they were on their knees, assaulted by the relentless torrent of warm water. He pulled out of her dribbling mouth and landed atop her heaving breast.

“Hah, Hah, Hah...T-That was perfect.”

Her hoarse voice called to him through the haze of lustful stupor. He struggled to respond in some fitting way, and only erked out, “M-My pleasure.”

He tried to pull out of her ass, only for her to grab one of his nuts. “Yipe!”

“Perfect doesn’t mean it’s over,” she chided him. Her nails grazed and swirled around his nut, as if appraising the amount of sperm still within. Delia rolled them back until he was flat on the floor, with the busty momma atop him. His cock throbbed in her ass as he gazed at her wet, flawless form. “Besides, the night’s still young, isn’t it?”

_ ‘Best. Job. Ever.’ _

**Notes for the Chapter:**

> Well, it's finally over- nearly a month late but its finally, FINALLY over. It was a fun romp and who knows - maybe I'll give something like this a crack again sometime...maybe not though XD. Anyway, hope you all enjoyed and keep enjoying my stuff, and please feel free to leave a comment or even head over to the Discord just to drop by. Until next time :)


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